2-Chloro-6-methylbenzoic acid → HCID 68969830, compound

HRID 1726215Notes

Reaction equation

HRID 1726215 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:30])[CH2:27][CH2:28][NH2:29])[CH2:22][CH2:21]2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)=[CH:6][CH:5]=1.[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:34]=1[C:35](O)=[O:36]>>[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:34]=1[C:35]([NH:29][CH2:28][CH2:27][CH:26]([N:23]1[CH2:22][CH2:21][CH:20]([N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:2])=[O:31])=[CH:9][CH:8]=2)[CH2:25][CH2:24]1)[CH3:30])=[O:36]

Participants

3

Reactant 2

HCID 888702-Chloro-6-methylbenzoic acidHCID 68968569HCID 68968569, compound

Product 1

HCID 68969830HCID 68969830, compound

Procedure

Using general procedure E with 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(3-cyano-benzyl)-amino]-benzoic acid methyl ester (see EXAMPLE 164) (73 mg, 0.17 mmol) and 2-chloro-6-methylbenzoic acid (43 mg, 0.25 mmol) followed by general procedure K with the resulting ester gave 4-[{1-[3-(2-chloro-6-methyl-benzoylamino)-1-methyl-propyl]-piperidin-4-yl}-(3-cyano-benzyl)-amino]-benzoic acid as a beige solid (44.5 mg, 46% over 2 steps).

Sources & evidence

ORD record
ord-d96b23b6a74b40f88b5d7d286853e2b2
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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