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Cesium carbonate → 2-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide

HRID 2036662
Notes
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Reaction equation

HRID 2036662 reaction equation
[NH2:1][C@H:2]([C:4]1[N:8]([CH:9]2[CH2:11][CH2:10]2)[C:7]2[C:12]([C:16]([NH:18][CH3:19])=[O:17])=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1)[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:26][C:27]1[S:28][C:29](Br)=[N:30][N:31]=1>CCO>[NH2:26][C:27]1[S:28][C:29]([NH:1][C@H:2]([C:4]2[N:8]([CH:9]3[CH2:10][CH2:11]3)[C:7]3[C:12]([C:16]([NH:18][CH3:19])=[O:17])=[CH:13][CH:14]=[CH:15][C:6]=3[N:5]=2)[CH3:3])=[N:30][N:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 36508832-Amino-5-bromo-1,3,4-thiadiazoleHCID 58459136(S)-2-(1-aminoethyl)-1-cyclopropyl-N-methyl-1H-benzo[d]imidazole-7-carboxamide

Product 1

HCID 584591982-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

A mixture of (S)-2-(1-aminoethyl)-1-cyclopropyl-N-methyl-1H-benzo[d]imidazole-7-carboxamide (prepared in example 20) (63.5 mg, 0.25 mmol), cesium carbonate (80 mg, 0.25 mmol) and 2-amino-5-bromo-[1,3,4]thiadiazole (44.3 mg, 0.25 mmol) in EtOH (5 mL) under N2 was stirred at rt for 18 h. The reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by flash chromatography over silica gel, using 0 to 10% gradient of MeOH in DCM with 0.2% NH4OH as eluent to give 2-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide: 1H NMR (400 MHz, DMSO-d6) δ 8.46-8.39 (1H, m); 7.62 (1H, d, J=8.0 Hz), 7.44 (1H, d, J=8.0 Hz), 7.24-7.16 (2H, m); 6.22 (2H, s), 5.46-5.37 (1H, m), 3.40-3.30 (1H, m), 2.82 (3H, d, J=4.0 Hz), 1.55 (3H, d, J=4.0 Hz), 1.22-1.15 (1H, m), 1.12-1.04 (1H, m), 1.01-0.92 (1H, m), 0.83-0.74 (1H, m); LC-MS (ESI) m/z 358.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography over silica gel

Sources & evidence

ORD record
ord-ec6c36cc856a464e9a683f8c706adc11
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575183B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes