t-Butyl 4-[(6-cyano-1-methyl-2-indolyl)carbonylamino]phenoxyacetate → t-Butyl 4-[(6-amidino-1-methyl-2-indolyl)carbonylamino]phenoxyacetate

HRID 1291001Notes

Reaction equation

C(C1C=C2C(C=C(C(O)=O)N2C)=CC=1)#[N:2].NC1C=CC(OCC(OC(C)(C)C)=O)=CC=1.[C:32]([C:34]1[CH:42]=[C:41]2[C:37]([CH:38]=[C:39]([C:44]([NH:46][C:47]3[CH:61]=[CH:60][C:50]([O:51][CH2:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[CH:49][CH:48]=3)=[O:45])[N:40]2[CH3:43])=[CH:36][CH:35]=1)#[N:33]>>[C:32]([C:34]1[CH:42]=[C:41]2[C:37]([CH:38]=[C:39]([C:44]([NH:46][C:47]3[CH:61]=[CH:60][C:50]([O:51][CH2:52][C:53]([O:55][C:56]([CH3:57])([CH3:58])[CH3:59])=[O:54])=[CH:49][CH:48]=3)=[O:45])[N:40]2[CH3:43])=[CH:36][CH:35]=1)(=[NH:2])[NH2:33]

Participants

Reactant 3

HCID 10763801t-Butyl 4-[(6-cyano-1-methyl-2-indolyl)carbonylamino]phenoxyacetate

HCID 107980776-cyano-1-methyl-1H-indole-2-carboxylic acid

HCID 22060435Tert-butyl 2-(4-aminophenoxy)acetate

Product 1

HCID 10598318t-Butyl 4-[(6-amidino-1-methyl-2-indolyl)carbonylamino]phenoxyacetate

Procedure

In the same manner as in Example 1 (2), 6-cyano-1-methyl-2-indolcarboxylic acid (52 mg, 0.26 mmol) and t-butyl 4-aminophenoxyacetate (63 mg, 0.29 mmol) were condensed to quantitatively give 109 mg of t-butyl 4-[(6-cyano-1-methyl-2-indolyl)carbonylamino]phenoxyacetate as a colorless solid.

Sources & evidence

ORD record: ord-67e2bbf8f4814ee4a3e4fcb7022d2193
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753670

Reaction notes

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