4-[6-(Cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic acid → 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 1904471Notes

Reaction equation

HRID 1904471 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([O:53][C:54]([NH:56][C:57]2[CH:65]=[C:64]3[C:60]([CH:61]=[N: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: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]([CH2:66][N:63]3[C:64]4[C:60](=[CH:59][CH:58]=[C:57]([NH:56][C:54]([O:53][CH:48]5[CH2:52][CH2:51][CH2:50][CH2:49]5)=[O:55])[CH:65]=4)[CH:61]=[N:62]3)=[C:14]([O:39][CH3:40])[CH:13]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 147087514-[6-(Cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic acidHCID 867431194-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

Product 1

HCID 883972444-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydrideYield 96%

Procedure

Using a procedure similar to part (f) of Example 4, but using 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic acid (N) instead of acid (J), there was obtained 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride (K) as a pink solid (2.14 g, 96%); partial NMR: (80 MHz, DMSO-d6): 3.86(s, 3H, OCH3), 5.49(s, 2H, ArCH2N), 7.42(s, 10H, NArH), 9.69(s, 1H, CONH).

Sources & evidence

ORD record
ord-3566c3decc944fc2a1ba0676b937469d
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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