Hydrochloric Acid → HCID 178478758, compound

HRID 424503Notes

Reaction equation

HRID 424503 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][S:11][C:10]3[CH:14]=[C:15]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[NH:20])[CH:16]=[CH:17][C:9]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:26].CCOCC>CO>[ClH:26].[ClH:26].[N:1]1([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][S:11][C:10]3[CH:14]=[C:15]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[NH:20])[CH:16]=[CH:17][C:9]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178511900HCID 178511900, compound

Product 1

HCID 178478758HCID 178478758, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(4-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)thiophene-2-carboximidamide (0.3524 g, 0.946 mmol) in MeOH (2 mL) was added 1M HCl in ether (4.73 mL, 4.73 mmol) at room temperature. The mixture was stirred for 5 minutes under argon atmosphere and was then concentrated to give a yellow foam (0.646 g, quantitative). 1H NMR (DMSO-d6) δ 11.51 (s, 1H), 11.23 (s, 1H), 9.68 (s, 1H), 8.69 (s, 1H), 8.15-8.11 (m, 2H), 7.37-7.34 (m, 1H), 7.08 (d, J=9.3 Hz, 1H), 7.00 (d, J=8.4 Hz, 1H), 3.81-3.76 (m. 2H), 3.66-3.64 (m, 2H), 3.56-3.46 (m, 2H), 3.33-3.30 (m, 2H), 3.13-3.10 (m, 2H), 3.06-3.00 (m, 2H), 2.00-1.86 (m, 4H); ESI-MS (m/z, %): 375, 373 (MH+, free base, 66), 278, 276 (100), 98 (21); HRMS (C19H25N4S2, MH+, Free base): calculated: 373.1515, observed: 373.1518. HPLC: 98% by area.

Workup

  1. concentrationwas then concentrated
  2. customto give a yellow foam (0.646 g, quantitative)

Sources & evidence

ORD record
ord-f8c78066edb943a59d71c99932e7e06d
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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