Hydrochloric Acid → HCID 11597706, compound

HRID 230743Notes

Reaction equation

HRID 230743 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12](=[S:37])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:28]4[CH:27]=[CH:26][N:25]=[C:24]([NH:29]C(=O)OC(C)(C)C)[C:23]=4[CH:22]=[CH:21]3)=[CH:16][CH:15]=2)=[O:10])=[CH:4][CH:3]=1.[ClH:38]>O1CCOCC1>[ClH:38].[NH2:29][C:24]1[C:23]2[CH:22]=[CH:21][N:20]([C:17]3[CH:16]=[CH:15][C:14]([NH:13][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[S:37])=[CH:19][CH:18]=3)[C:28]=2[CH:27]=[CH:26][N:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57763161HCID 57763161, compound

Product 1

HCID 11597706HCID 11597706, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 1-(4-(3-(2-(4-fluorophenyl)acetyl)thioureido)phenyl)-1H-pyrrolo[3,2-c]pyridin4-ylcarbamate (10 mg, 0.19 mmol) was treated with 4 N HCl in dioxane (2 mL) and stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the remaining solid was triturated twice with EtOAc (˜0.5 mL) to afford the title compound as the hydrochloride salt (6.5 mg, 74%). 1H NMR (DMSO-d6) δ 12.48 (s, 1H), 11.80 (s, 1H), 8.42 (br s, 2H), 7.88 (d, 2H, J=8.5 Hz), 7.78 (d, 1H, J=3.1 Hz), 7.64-7.55 (m, 3H), 7.38 (dd, 2H, J=7.6, 6.2 Hz), 7.27 (d, 1H, J=3.1 Hz), 7.18 (t, 2H, J=9.7 Hz), 6.97 (d, 1H, J=7.0 Hz), 3.83 (s, 2H); LCMS (ESI+) m/z 420 (M+H)+; HPLC tR=3.42 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe remaining solid was triturated twice with EtOAc (˜0.5 mL)

Sources & evidence

ORD record
ord-8d618adc39ac4a77b2e352d4722e8cce
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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