HCID 68760588, 화합물 → (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 79579노트

반응식

HRID 79579 반응식
[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

참가 물질

3

반응물 1

HCID 68760588HCID 68760588, 화합물

생성물 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-one수율 50.4%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-01aa7f6355fd40faa3edc2dc6bbde12a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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