Hydrochloric Acid → 2-[3-(4-Chlorophenyl)ureido]-6-(cyclopropylmethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide hydrochloride

HRID 1483202Notes

Reaction equation

HRID 1483202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[NH:10][C:11]2[S:23][C:14]3[CH2:15][N:16]([CH2:19][CH:20]4[CH2:22][CH2:21]4)[CH2:17][CH2:18][C:13]=3[C:12]=2[C:24]([NH2:26])=[O:25])=[CH:4][CH:3]=1.Cl>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:27])[NH:10][C:11]2[S:23][C:14]3[CH2:15][N:16]([CH2:19][CH:20]4[CH2:21][CH2:22]4)[CH2:17][CH2:18][C:13]=3[C:12]=2[C:24]([NH2:26])=[O:25])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1182705102-[3-(4-Chlorophenyl)ureido]-6-(cyclopropylmethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

Product 1

HCID 1182705092-[3-(4-Chlorophenyl)ureido]-6-(cyclopropylmethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide hydrochlorideYield 142.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound A5 (121 mg, 0.299 mmol) in tetrahydrofuran (5 mL) was added hydrochloride (2 M in diethyl ether, 0.200 mL, 0.400 mmol). After stirring at room temperature for 15 min, the reaction mixture was concentrated under reduced pressure and the resulting residue was triturated with methylene chloride to afford compound A6 as a yellow solid (94 mg, 71%): 1H NMR (500 MHz, DMSO-d6) δ 10.97 (s, 1H), 10.28 (bs, 1H), 10.26 (s, 1H), 7.55-7.48 (m, 3H), 7.35 (d, J=9.0 Hz, 2H), 7.14 (bs, 1H), 4.61-4.57 (m, 1H), 4.31-4.28 (m, 1H), 3.72-3.70 (m, 1H), 3.39-3.36 (m, 1H), 3.22-3.19 (m, 1H), 3.11-3.08 (m, 3H), 1.19-1.11 (m, 1H), 0.70-0.63 (m, 2H), 0.45-0.39 (m, 2H). MS (M+H) 405.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was triturated with methylene chloride

Sources & evidence

ORD record
ord-21b95aeb9e5f4baaad74f53f740f0b80
Source dataset
uspto-grants-2016_08
Patent number
US09416141B2

Reaction notes

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