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Triphenylphosphine → 6-(4-(4-(aminomethyl)-4-methoxypiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1038810
ノート
印刷プレビュー

反応式

HRID 1038810 の反応式
[N:1]([CH2:4][C:5]1([O:34][CH3:35])[CH2:10][CH2:9][N:8]([C:11]2[C:12]3[O:33][CH:32]=[CH:31][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:30]=[CH:29][C:21]4[O:22][C:23]([CH3:28])([CH3:27])[C:24](=[O:26])[NH:25][C:20]=4[CH:19]=3)[N:16]=2)[CH2:7][CH2:6]1)=[N+]=[N-].N(CC1(OC)CCN(C(OC(C)(C)C)=O)CC1)=[N+]=[N-].ClC1N=C(Cl)C2OC=CC=2N=1.NC1C=CC2OC(C)(C)C(=O)NC=2C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]1([O:34][CH3:35])[CH2:6][CH2:7][N:8]([C:11]2[C:12]3[O:33][CH:32]=[CH:31][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:30]=[CH:29][C:21]4[O:22][C:23]([CH3:27])([CH3:28])[C:24](=[O:26])[NH:25][C:20]=4[CH:19]=3)[N:16]=2)[CH2:9][CH2:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 11776TriphenylphosphineHCID 136654966-Amino-2,2-dimethyl-2H-benzo[B][1,4]oxazin-3(4H)-oneHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 58504149Tert-butyl 4-(azidomethyl)-4-methoxypiperidine-1-carboxylateHCID 866650986-(4-(4-(azidomethyl)-4-methoxypiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

生成物 1

HCID 68750633
6-(4-(4-(aminomethyl)-4-methoxypiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one
収率 76%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6-(4-(4-(azidomethyl)-4-methoxypiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.030 g, 0.063 mmol, prepared using C from tert-butyl 4-(azidomethyl)-4-methoxypiperidine-1-carboxylate [WO 2010/080864, Example 257], A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with 6-amino-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one [ArkPharm]) and triphenylphosphine (0.025 g, 0.094 mmol) in THF (16 mL) and water (2 mL) was stirred at about 100° C. overnight. The organic phase was removed and diluted with water. The aqueous phase was neutralized with aqueous 2 N NaOH and extracted with EtOAc. The combined organic phase was washed with brine and dried over Na2SO4, filtered, concentrated under vacuum and purified by HPLC (Table 2, Method v) to afford 6-(4-(4-(aminomethyl)-4-methoxypiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.022 g, 76%). LC/MS (Table 2, method h) Rt=1.77 min.; MS m/z: 453 (M+H)+. Syk IC50=A

後処理

  1. customprepared
  2. customThe organic phase was removed
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. custompurified by HPLC (Table 2, Method v)

出典と根拠

ORDレコード
ord-85d6e2b468ea4ef6ad395896e46bcecf
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08551981B2

反応ノート

読み込み中…

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