3-(Trifluoromethyl)benzoic acid → N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-3-(trifluoromethyl)-benzamide

HRID 1244967Notes

Reaction equation

HRID 1244967 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:13]=[C:12]([Cl:14])[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:43][C:44]([F:55])([F:54])[C:45]1[CH:46]=[C:47]([CH:51]=[CH:52][CH:53]=1)[C:48](O)=[O:49]>ClCCl.O>[Cl:14][C:12]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:48](=[O:49])[C:47]2[CH:51]=[CH:52][CH:53]=[C:45]([C:44]([F:43])([F:54])[F:55])[CH:46]=2)[N:13]=1

Participants

7

Reactant 4

HCID 99633-(Trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 21922944N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-3-(trifluoromethyl)-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

280 mg of the product obtained in Stage 1 of Example 7, 203 mg of 1-hydroxybenzotriazole hydrate, 287 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 4 ml of dichloromethane are mixed together, 230 mg of 3-trifluoromethyl benzoic acid is added and agitation is carried out for 6 hours and 30 minutes at ambient temperature. Water is added, followed by separating, washing with ether, drying and 307 mg of expected product is collected.

Workup

  1. customby separating
  2. washwashing with ether
  3. customdrying
  4. custom307 mg of expected product is collected

Sources & evidence

ORD record
ord-a38c8a512e334701b9ea43f08746191c
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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