Hydrochloric Acid → HCID 67156256, compound

HRID 2196686Notes

Reaction equation

HRID 2196686 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:15]3[NH:41][C:18]4=[N:19][CH:20]=[C:21]([NH:23][C:24](=[O:40])[C:25]5[C:30]([F:31])=[CH:29][CH:28]=[C:27]([NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])[C:26]=5[F:39])[CH:22]=[C:17]4[CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:4][O:3]1.Cl>C1COCC1.CO>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[NH:41][C:18]3=[N:19][CH:20]=[C:21]([NH:23][C:24](=[O:40])[C:25]4[C:30]([F:31])=[CH:29][CH:28]=[C:27]([NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])[C:26]=4[F:39])[CH:22]=[C:17]3[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67155755HCID 67155755, compound

Product 1

HCID 67156256HCID 67156256, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of N-(2-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (22 mg, 36 mmol) in 2:1 THF/MeOH (3 mL) was treated with 1N HCl (1 mL) and the mixture stirred at room temperature for 16 hours. The volatiles were removed via rotary evaporation, and the resulting residue was partitioned between EtOAc and aqueous NaHCO3. The layers were separated, and the organic layer was dried (MgSO4), filtered and concentrated to a solid. The solid was triturated with DCM and collected via vacuum filtration to afford N-(2-(3-(2,3-dihydroxypropoxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (13 mg, 64%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.16 (s, 1H), 10.89 (s, 1H), 9.80 (s, 1H), 8.40-8.33 (m, 2H), 7.58-7.49 (m, 3H), 7.40-7.34 (m, 1H), 7.31-7.24 (m, 1H), 7.00-6.90 (m, 2H), 5.00-4.96 (m, 1H), 4.72-4.67 (m, 1H), 4.12-4.07 (m, 1H), 4.01-3.99 (m, 1H), 3.88-3.81 (m, 1H), 3.52-3.47 (m, 1H), 3.16-3.10 (m, 2H), 1.82-1.74 (m, 2H), 1.04-0.97 (m, 3H); m/z (APCI-pos) M+1=561.2.

Workup

  1. customThe volatiles were removed via rotary evaporation
  2. customthe resulting residue was partitioned between EtOAc and aqueous NaHCO3
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. customThe solid was triturated with DCM
  8. filtrationcollected via vacuum filtration

Sources & evidence

ORD record
ord-9bc44e65f74441b684be1fe4e6a98c35
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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