4-[6-(2-Cyclopentyl-acetylamino)-indol-1-ylmethyl]-3-methoxy-benzoic acid → 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 1904473Notes

Reaction equation

HRID 1904473 reaction equation
[C:1]1([N:7]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:8]([O:10][C:11](=[O:41])[C:12]2[CH:17]=[CH:16][C:15](CC3C4C(=CC=C(NC(=O)CC5CCCC5)C=4)N(CC)C=3)=[C:14]([O:39][CH3:40])[CH:13]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:48]1([CH2:53][C:54]([NH:56][C:57]2[CH:65]=[C:64]3[C:60]([CH:61]=[CH:62][N:63]3[CH2:66]C3C=CC(C(O)=O)=CC=3OC)=[CH:59][CH:58]=2)=[O:55])[CH2:52][CH2:51][CH2:50][CH2:49]1>>[C:1]1([N:7]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:8]([O:10][C:11](=[O:41])[C:12]2[CH:17]=[CH:16][C:15]([CH2:66][N:63]3[C:64]4[C:60](=[CH:59][CH:58]=[C:57]([NH:56][C:54](=[O:55])[CH2:53][CH:48]5[CH2:49][CH2:50][CH2:51][CH2:52]5)[CH:65]=4)[CH:61]=[CH:62]3)=[C:14]([O:39][CH3:40])[CH:13]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 147087384-[6-(2-Cyclopentyl-acetylamino)-indol-1-ylmethyl]-3-methoxy-benzoic acidHCID 867431194-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

Product 1

HCID 883972314-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydrideYield 92%

Procedure

Using a procedure similar to part (f) of Example 4, but using 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoic acid (Q) instead of acid (J), there was obtained 4-[6-(2-cyclopentylacetamido)indol-1-ylmethyl]-3-methoxybenzoic N,N-diphenyl carbamic anhydride (O) as an off-white powder (1.4 g, 92%); partial NMR: (80 MHz, DMSO-d6): 3.98(s, 3H, OCH3) 5.30(s, 2H, NCH2Ar), 7.40(s, 10H, NArH), 9.69(s, 1H, CONH).

Sources & evidence

ORD record
ord-6211bcb0fc354ccaacdf5c04178a0386
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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