Prop-2-en-1-yl 4-aminobenzoate → 4-[({(2S,4R)-1-[(3-chloro-4-fluoro-1-methyl-1H-indol-5-yl)carbonyl]-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinyl}carbonyl)amino]benzoic acid

HRID 1053847Notes

Reaction equation

HRID 1053847 reaction equation
CC(O[C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]2[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:23]([OH:25])=[O:24])=[O:7])(C)C.[NH2:26][C:27]1[CH:38]=[CH:37][C:30]([C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])=[CH:29][CH:28]=1.[Cl:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:50]([OH:52])=O)[C:47]=2[F:49])[N:42]([CH3:53])[CH:41]=1>[Pd]>[Cl:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:6]([N:8]3[CH2:12][C@@H:11]([CH:13]4[CH2:14][CH2:15][N:16]([S:19]([CH3:22])(=[O:20])=[O:21])[CH2:17][CH2:18]4)[CH2:10][C@H:9]3[C:23]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])=[CH:37][CH:38]=3)=[O:25])=[O:7])[C:47]=2[F:49])[N:42]([CH3:53])[CH:41]=1.[Cl:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:50]([N:8]3[CH2:12][C@@H:11]([CH:13]4[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]4)[CH2:10][C@H:9]3[C:23]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:37][CH:38]=3)=[O:24])=[O:52])[C:47]=2[F:49])[N:42]([CH3:53])[CH:41]=1

Participants

6

Reactant 3

HCID 13075143Prop-2-en-1-yl 4-aminobenzoateHCID 900232723-chloro-4-fluoro-1-methyl-1H-indole-5-carboxylic acidHCID 118107723(2S,4R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinecarboxylic acid

Product 2

HCID 725508474-[({(2S,4R)-1-[(3-chloro-4-fluoro-1-methyl-1H-indol-5-yl)carbonyl]-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinyl}carbonyl)amino]benzoic acidHCID 90033600Allyl 4-[({(2S,4R)-1-[(3-chloro-4-fluoro-1-methyl-1H-indol-5-yl)carbonyl]-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinyl}carbonyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Allyl 4-[({(2S,4R)-1-[(3-chloro-4-fluoro-1-methyl-1H-indol-5-yl)carbonyl]-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinyl}carbonyl)amino]benzoate was prepared from the compound prepared in Example 63 following the procedures described in Example 5, 9 and 8. (Note: in the step corresponding to Example 5, allyl 4-aminobenzoate was used in place of tert-butyl 4-aminobenzoate. In the step corresponding to Example 8, the acid prepared in Example 92 was used in place of 1-(N,N′-bis(tert-butoxycarbonyl)carbamimidoyl)piperidine-4-carboxylic acid). After that, the crude allyl ester was treated with palladium(0) following the procedure described in Example 91 to give the title compound as an off-white solid.

Sources & evidence

ORD record
ord-b6e3c416b2514bc19c95071301af0bcc
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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