Diethylamine → 3-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1-propyl-1H-indole-2-carboxylic acid bis-cyclopropylmethyl-amide

HRID 1911790Notes

Reaction equation

HRID 1911790 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH2:24][CH2:25][CH3:26])[C:16]=1[C:27]([OH:29])=O)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH:39]1([CH2:42][NH:43][CH2:44][CH:45]2[CH2:47][CH2:46]2)[CH2:41][CH2:40]1.FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CN(CC1C2C(=CC=CC=2)NC=1C(O)=O)C1N=NN(C)N=1.C(NCC)C>>[CH:39]1([CH2:42][N:43]([CH2:44][CH:45]2[CH2:47][CH2:46]2)[C:27]([C:16]2[N:17]([CH2:24][CH2:25][CH3:26])[C:18]3[C:23]([C:15]=2[CH2:14][N:7]([CH2:6][C:5]2[CH:30]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:32]=[C:3]([C:2]([F:38])([F:1])[F:37])[CH:4]=2)[C:8]2[N:9]=[N:10][N:11]([CH3:13])[N:12]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:29])[CH2:41][CH2:40]1

Participants

5

Reactant 4

HCID 8021DiethylamineHCID 15284719Bis(cyclopropylmethyl)amineHCID 574444253-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1-propyl-1H-indole-2-carboxylic acidHCID 574444593-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1H-indole-2-carboxylic acid

Product 1

HCID 237293313-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1-propyl-1H-indole-2-carboxylic acid bis-cyclopropylmethyl-amide

Procedure

3-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1-propyl-1H-indole-2-carboxylic acid (0.16 g, 0.29 mmol) and bis cyclopropylmethylamine (0.37 g, 0.29 mmol) were used to synthesize the title compound instead of using 3-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1H-indole-2-carboxylic acid and diethylamine in step (ii) of example 131 (0.08 g, 42%)

Sources & evidence

ORD record
ord-f465276cba9c46c1b4c83e5ad57c5e88
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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