2,6-Di-tert-butyl-4-methylpyridine → [(1R,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2-hydroxycyclopentyl]methyl sulfamate

HRID 1677925ノート

反応式

HRID 1677925 の反応式
[C@@H:1]1([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH:17][C@H:18]3[CH2:22][C@H:21]([OH:23])[C@@H:20]([CH2:24][OH:25])[CH2:19]3)[CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.Cl[S:42]([NH:45]C(=O)OC(C)(C)C)(=[O:44])=[O:43]>C(#N)C>[S:42](=[O:44])(=[O:43])([O:25][CH2:24][C@H:20]1[CH2:19][C@@H:18]([NH:17][C:13]2[CH:12]=[C:11]([NH:10][C@@H:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)[N:16]=[CH:15][N:14]=2)[CH2:22][C@@H:21]1[OH:23])[NH2:45]

参加物

5

反応物 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 66797896(1S,2R,4R)-4-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-(hydroxymethyl)cyclopentanol

生成物 1

HCID 24829705[(1R,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2-hydroxycyclopentyl]methyl sulfamate収率 40.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A neat mixture of (1S,2R,4R)-4-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-(hydroxymethyl)cyclopentanol (100. mg, 0.294 mmol) and 2,6-di-tert-butyl-4-methylpyridine (181 mg, 0.881 mmol) was dissolved in ACN (5.00 mL) before tert-butyl (chlorosulfonyl)carbamate (95.0 mg, 0.441 mmol, as prepared in Example 21c) was added. The reaction was stirred for 2 h before being quenched via addition of MeOH (2 mL). The resulting mixture was concentrated in vacuo and purified via silica gel chromatography eluting with a gradient of 10 to 20% MeOH in DCM to afford the title compound as an amorphous solid (50.0 mg, 33%). LC/MS: Rt=1.24 min, ES+ 520. (AA standard).

後処理

  1. additionwas added
  2. custombefore being quenched via addition of MeOH (2 mL)
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. custompurified via silica gel chromatography
  5. washeluting with a gradient of 10 to 20% MeOH in DCM

出典と根拠

ORDレコード
ord-4a05b46a9084475baa2cf3801c1bae45
出典データセット
uspto-grants-2011_08
特許番号
US08008307B2

反応ノート

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