Hydrochloric Acid → Hydrochloric Acid

HRID 1790085Notes

Reaction equation

HRID 1790085 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:27])[NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][N:15]2[CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)(C)(C)C.[ClH:29]>ClCCl>[NH2:7][CH2:8][C:9]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][N:15]2[CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:27].[ClH:29]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69652714{[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidHCID 220366182-amino-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{[1-(2-Pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (1.00 g, 2.58 mmol) and a solution of HCl (5 mL, 4M in dioxane) was in dichloromethane (30 mL) was stirred for 3 hours. The mixture was filtered and rinsed with dichloromethane to provide the title compound as the bis-HCl salt. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.78–2.00 (m, 4H), 2.88–3.00 (m, 2H), 3.45 (m, 2H), 3.67 (m, 2H), 4.09 (m, 2H), 4.85 (t, 2H, J=6.45), 7.40–7.77 (m, 3H), 8.30 (s, 3H), 8.59 (s, 1H), 10.9 (s, 1H), 11.11 (s, 1H); MS (DCI/NH3) m/z 288 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washrinsed with dichloromethane

Sources & evidence

ORD record
ord-69fbdde797e440e99803ed6e568027ab
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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