Triethylamine → HCID 23537349, compound

HRID 1792596Notes

Reaction equation

HRID 1792596 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]3[CH:16]=[C:17]([C:20]4[CH:21]=[N:22][N:23]([C:25]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:24]=4)[CH:18]=[CH:19][C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:44][C:45]1[S:46][CH:47]=[C:48]([CH3:50])[N:49]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH3:50][C:48]1[N:49]=[C:45]([NH:44][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([C:11]3[N:15]4[CH:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([C:25]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)([C:38]6[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=6)[C:26]6[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=6)[CH:24]=5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)=[CH:10][C:2]=2[F:1])[S:46][CH:47]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 741432-Amino-4-methylthiazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22032217HCID 22032217, compound

Product 1

HCID 23537349HCID 23537349, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

170 mg 2-fluoro-4-[6-(1-trityl-1H-4-pyrazolyl)imidazo-[1,2-a]pyridin-3-yl]benzoic acid (compound in Example 472) and 34.4 mg 2-amino-4-methyl-1,3-thiazole were allowed to react overnight with 146 mg benzotriazol-1-yloxy-tris-(dimethylamino)phosphonium hexafluorophosphate and 50 μL triethylamine in 6 mL dichloromethane. The reaction solution was purified by an NH silica gel column, to give 169 mg of the title compound as colorless crystals (recrystallization solvent: ethyl acetate).

Workup

  1. customThe reaction solution was purified by an NH silica gel column

Sources & evidence

ORD record
ord-5ebccfcfbcdc44148db4c42f0d9dc9ea
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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