Hydrochloric Acid → 2-Thiazolamine, 4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-

HRID 1754762Notes

Reaction equation

HRID 1754762 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([CH2:14][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[N:17]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:16]=2)=[C:11]([Cl:13])[N:12]=1)(C)(C)C.Cl>ClCCl>[C:28]1([S:25]([N:17]2[C:18]3=[N:19][CH:20]=[C:21]([Cl:24])[CH:22]=[C:23]3[C:15]([CH2:14][C:10]3[S:9][C:8]([NH2:7])=[N:12][C:11]=3[Cl:13])=[CH:16]2)(=[O:27])=[O:26])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57619385Carbamic acid, N-[4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-2-thiazolyl]-, 1,1-dimethylethyl ester

Product 1

HCID 576193502-Thiazolamine, 4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-Yield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [5-(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-4-chloro-thiazol-2-yl]-carbamic acid tert-butyl ester (591, 4.30 g, 7.97 mmol) in dichloromethane (70.0 mL) was added a solution of hydrogen chloride (4.00 M in 1,4-dioxane, 42.0 mL). The reaction was stirred at room temperature for 2 days, then concentrated, and triturated with ethyl ether and ethyl acetate to give the desired compound (592, 2.60 g, 74.2%). MS (ESI) [M+H+]+=439.0.

Workup

  1. concentrationconcentrated
  2. customtriturated with ethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-8ae3ad3b82c645fb9fee097e090f3999
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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