HCID 68764146, compound → HCID 44199251, compound

HRID 79576Notes

Reaction equation

HRID 79576 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:21](=[O:43])[N:22]2[CH2:27][CH2:26][N:25]([C:28]3[C:33]([C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[CH:32][N:31]=[C:30]4[NH:40][CH:41]=[CH:42][C:29]=34)[CH2:24][CH2:23]2)[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:7]=[CH:6][C:5]([C@@H:8]([CH2:9][NH:10][CH:18]([CH3:20])[CH3:19])[C:21]([N:22]2[CH2:27][CH2:26][N:25]([C:28]3[C:33]([C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[CH:32][N:31]=[C:30]4[NH:40][CH:41]=[CH:42][C:29]=34)[CH2:24][CH2:23]2)=[O:43])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68764146HCID 68764146, compound

Product 1

HCID 44199251HCID 44199251, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-tert-Butyl 2-(4-chlorophenyl)-3-oxo-3-(4-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propyl(isopropyl)carbamate (25 mg, 0.041 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-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (16 mg, 77% yield) trihydro chloride. 1H NMR (400 MHz, DMSO-d6) δ 12.40 (br s, 1H), 8.96 (s, 1H), 8.77 (d, 1H), 8.45 (m, 1H), 8.13 (s, 1H), 7.89-7.84 (m, 1H), 7.52-7.45 (m, 3H), 7.41-7.32 (m, 3H), 6.74 (s, 1H), 4.66-4.61 (m, 1H), 3.90-3.15 (m, 10H), 3.00-2.96 (m, 1H), 2.82-2.75 (m, 1H), 1.23 (dq, 6H); m/z (APCI pos) 503.3 (100%) [M].

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-86801d2984704ed3bfa42ec0daaee4b4
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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