HCID 68760588, compound → (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 79579Notes

Reaction equation

HRID 79579 reaction equation
[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

Participants

3

Reactant 1

HCID 68760588HCID 68760588, compound

Product 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-oneYield 50.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-01aa7f6355fd40faa3edc2dc6bbde12a
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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