Sodium Bicarbonate → HCID 72943989, compound

HRID 531580Notes

Reaction equation

HRID 531580 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:28]([C:29]5[C:30]([CH3:43])=[N:31][N:32]([CH2:35][C:36]6[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=6)[C:33]=5[CH3:34])=[C:27]([CH:44]5[CH2:46][CH2:45]5)[N:26](C(OC(C)(C)C)=O)[C:23]4=[N:24][CH:25]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CO.Cl.C(=O)(O)[O-].[Na+]>CO.C(Cl)(Cl)Cl>[CH:44]1([C:27]2[NH:26][C:23]3=[N:24][CH:25]=[C:20]([C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:15][CH:16]=4)[CH:21]=[C:22]3[C:28]=2[C:29]2[C:30]([CH3:43])=[N:31][N:32]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=3)[C:33]=2[CH3:34])[CH2:46][CH2:45]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 90031536HCID 90031536, compound

Product 1

HCID 72943989HCID 72943989, compoundYield 9.72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (100 mg) dissolved in 2 ml of methanol and added methanol/HCl (3 ml) at 0° C. and stirred at room temperature for 30 min. The reaction was monitored by TLC (10% methanol in chloroform). The reaction mixture was concentrated under reduced pressure to afford crude product. The residue was basified with saturated sodium bicarbonate solution and extracted with DCM (2×25 ml). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 7 mg (9.72% yield) of the pure required product. 1H NMR (DMSO-d6, 400 MHz): δ 11.30 (s, 1H), 8.34 (s, 1H), 7.64-7.39 (m, 5H), 7.15-7.11 (t, 1H), 7.01-6.95 (m, 4H), 5.34 (s, 2H), 4.20-4.00 (m, 4H), 3.10-3.00 (m, 4H), 2.09 (s, 3H), 2.08 (s, 3H), 1.82-1.79 (m, 1H), 0.96-0.95 (m, 4H). MS: m/z=521.4 (M+1), HPLC Purity: 80.32% Method: A.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford crude product
  3. extractionextracted with DCM (2×25 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-696cfc3022ba4c2c954a0d02b6c54051
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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