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

HRID 1483210Notes

Reaction equation

HRID 1483210 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:25])[NH:10][C:11]2[S:21][C:14]3[CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH2:18][C:13]=3[C:12]=2[C:22]([NH2:24])=[O:23])=[CH:4][C:3]=1[CH3:26].Cl>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:25])[NH:10][C:11]2[S:21][C:14]3[CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH2:18][C:13]=3[C:12]=2[C:22]([NH2:24])=[O:23])=[CH:4][C:3]=1[CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1182701022-[3-(4-Chloro-3-methylphenyl)ureido]-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

Product 1

HCID 1182701012-[3-(4-Chloro-3-methylphenyl)ureido]-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of compound F5 (157 mg, 0.400 mmol) in methylene chloride (50 mL) at room temperature was added hydrochloride (2 M in diethyl ether, 0.300 mL, 0.600 mmol). After addition, the mixture was concentrated under reduced pressure. The resulting solid was triturated with methylene chloride and filtered to afford compound F6 as yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 10.94 (s, 1H), 10.84 (bs, 1H), 10.22 (s, 1H), 7.75-6.90 (m, 5H), 4.49 (d, J=14.5 Hz, 1H), 4.22-4.16 (m, 1H), 3.65-3.62 (m, 1H), 3.38-3.05 (m, 5H), 2.30 (s, 3H), 1.32 (t, J=7.2 Hz, 3H). MS (M+H) 393.

Workup

  1. additionAfter addition
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe resulting solid was triturated with methylene chloride
  4. filtrationfiltered

Sources & evidence

ORD record
ord-281e220871454608a059d8c248b75dcf
Source dataset
uspto-grants-2016_08
Patent number
US09416141B2

Reaction notes

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