Iodoacetamide → HCID 22180707, compound

HRID 1795875Notes

Reaction equation

HRID 1795875 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([NH2:19])=[C:12]2[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC[C:24]([NH2:26])=[O:25]>CCOCC.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:24](=[O:25])[NH2:26])[C:13]([NH2:19])=[C:12]2[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([NH2:19])=[C:12]2[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3727IodoacetamideHCID 22180710HCID 22180710, compound

Product 2

HCID 22180707HCID 22180707, compoundHCID 22180718HCID 22180718, compound

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

Using the general method of selective N-alkylation described for 5-benzyloxy-2-amino-1-methyl-1H-indole-3-carbonitrile in Example 25, using iodoacetamide (222 mg; 1.2 mmol), 5-benzyloxy-1-carbamoylmethyl-2-amino-1H-indole-3-carbonitrile (163 mg) was obtained as a white solid from 5-benzyloxy-2-amino-1H-indole-3-carbonitrile (263 mg; 1.0 mmol) after trituration with Et2O/CH2Cl2.

Sources & evidence

ORD record
ord-34e2c6004c0f425395a2bc37569ae3b3
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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