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

HRID 1911789Notes

Reaction equation

HRID 1911789 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=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]([CH3:24])[C:16]=1[C:25]([OH:27])=O)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH:37]1([CH2:40][NH:41][CH2:42][CH:43]2[CH2:45][CH2:44]2)[CH2:39][CH2:38]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:37]1([CH2:40][N:41]([CH2:42][CH:43]2[CH2:45][CH2:44]2)[C:25]([C:16]2[N:17]([CH3:24])[C:18]3[C:23]([C:15]=2[CH2:14][N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:36])[F:35])[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=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:27])[CH2:39][CH2:38]1

Participants

5

Reactant 4

HCID 8021DiethylamineHCID 15284719Bis(cyclopropylmethyl)amineHCID 574444243-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1-methyl-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 237293303-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1-methyl-1H-indole-2-carboxylic acid bis-cyclopropylmethyl-amideYield 62%

Procedure

3-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1-methyl-1H-indole-2-carboxylic acid (0.08 g, 0.156 mmol) and bis cyclopropylmethylamine (0.02 g, 0.156 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 (0.05 g, yield: 62%).

Sources & evidence

ORD record
ord-3a978419e31944cbb9c916730fe388e9
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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