1,1'-Carbonyldiimidazole → N-[(1S,2R)-2-aminocyclohexyl]-4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxamide

HRID 1253570Notes

Reaction equation

HRID 1253570 reaction equation
[CH3:1][O:2][C:3]1[N:8]2[C:9]([C:12]3[CH:13]=[C:14]([C:17]([OH:19])=O)[S:15][CH:16]=3)=[CH:10][N:11]=[C:7]2[CH:6]=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C@@H:38]1([NH2:45])[CH2:43][CH2:42][CH2:41][CH2:40][C@@H:39]1[NH2:44]>CN(C)C=O>[NH2:44][C@@H:39]1[CH2:40][CH2:41][CH2:42][CH2:43][C@@H:38]1[NH:45][C:17]([C:14]1[S:15][CH:16]=[C:12]([C:9]2[N:8]3[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:6][C:7]3=[N:11][CH:10]=2)[CH:13]=1)=[O:19]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3429171,2-Diaminocyclohexane, cis-HCID 584046854-(5-Methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylic acid

Product 1

HCID 58404654N-[(1S,2R)-2-aminocyclohexyl]-4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylic acid (10.0 mg, 0.029 mmol) in N,N-dimethylformamide (1 ml) was added 1,1′-carbonyldiimidazole (7.0 mg, 0.043 mmol). After 20 minutes cis-1,2-cyclohexanediamine (0.034 ml, 0.29 mmol) was added. After 10 minutes the reaction mixture was purified directly by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give N-[(1S,2R)-2-aminocyclohexyl]-4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxamide. 1H NMR (600 MHz, DMSO-d6) δ 8.13 (s, 1H); 7.85 (d, 2H); 7.74 (d, 1H); 7.59 (s, 1H); 7.54 (d, 1H); 7.47-7.49 (m, 2H); 7.38-7.41 (m, 1H); 6.66 (d, 1H); 3.99 (s, 3H); 1.50-1.72 (m, 7H); 1.29-1.36 (m, 3H). LRMS (ESI) calculated for C25H27N4O2S [M+H]+, 447.2 found 447.1.

Workup

  1. customAfter 10 minutes the reaction mixture was purified directly by preparative HPLC Reverse phase (C-18)
  2. washeluting with acetonitrile/water+0.05% TFA

Sources & evidence

ORD record
ord-6d3997cffa75454cb7a25f61c3a83ea7
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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