HCID 68760588、化合物 → (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one

HRID 79579ノート

反応式

HRID 79579 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[C:34]([C:35]4[O:36][C:37]([CH3:40])=[N:38][N:39]=4)=[CH:33][N:32]=[C:31]4[NH:41][CH:42]=[CH:43][C:30]=34)[CH2:25][CH2:24]2)=[O:22])[CH2:9][N:10]([CH:18]([CH3:20])[CH3:19])C(=O)OC(C)(C)C)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([CH2:9][NH:10][CH:18]([CH3:20])[CH3:19])[C:21]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[C:34]([C:35]4[O:36][C:37]([CH3:40])=[N:38][N:39]=4)=[CH:33][N:32]=[C:31]4[NH:41][CH:42]=[CH:43][C:30]=34)[CH2:27][CH2:28]2)=[O:22])=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 68760588HCID 68760588、化合物

生成物 1

HCID 44197714(S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one収率 50.4%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

(S)-tert-Butyl 2-(4-chlorophenyl)-3-(4-(5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (50 mg, 0.082 mmol) in TFA (3 mL) was stirred for 30 minutes and then concentrated to dryness. The resulting residue was dissolved in minimal DCM (0.2 mL) and added to 2N HCl in ether. The resulting solid was filtered and dried under nitrogen to yield (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (21 mg, 50% yield) hydrochloride as a solid. 1H NMR (400 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.84 (s, 1H), 8.35 (s, 2H), 7.52-7.48 (m, 2H), 7.46-4.42 (m, 1H), 7.40-7.36 (m, 2H), 6.64 (s, 1H), 4.58 (m, 1H), 3.70-3.20 (m, 10H), 3.01 (s, 1H), 2.78 (s, 1H), 2.54 (s, 3H), 1.24 (dq, 6H); MS ESI (+) m/z 508 detected.

後処理

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting residue was dissolved in minimal DCM (0.2 mL)
  3. additionadded to 2N HCl in ether
  4. filtrationThe resulting solid was filtered
  5. customdried under nitrogen

出典と根拠

ORDレコード
ord-01aa7f6355fd40faa3edc2dc6bbde12a
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

反応ノート

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