Dimethylamine → HCID 18706951, compound

HRID 1422116Notes

Reaction equation

HRID 1422116 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]2[N:8]3[C:9]([C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:24][CH:23]=4)=[CH:21][C:7]=13)=[C:10]1[C:18](=[O:19])[O:17][C:15](=[O:16])[C:11]1=2)(=[O:3])[CH3:2].[CH3:36][NH:37][CH3:38]>>[C:1]([O:4][CH2:5][C:6]1[C:7]2[N:8]3[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]([OH:17])=[O:16])=[C:10]([C:18](=[O:19])[N:37]([CH3:38])[CH3:36])[C:9]3=[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=1)[CH:21]=2)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 56622940HCID 56622940, compound

Product 1

HCID 18706951HCID 18706951, compoundYield 68%

Procedure

5-Acetoxymethyl-3-(4-benzyloxyphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid anhydride was reacted with dimethylamine by the general synthetic principles outlined in example 62, step 9, to afford 5-acetoxymethyl-3-(4-benzyloxyphenyl)-2-dimethylcarbamoylpyrrolo[2,1,5-cd]indolizine-1-carboxylic acid as crystals in 68% yield. 1H-NMR (DMSO-d6, 300 MHz) δ: 2.22 (s, 3H); 2.72 (s, 3H); 3.08 (s, 3H); 5.20 (s, 2H); 5.70 (s, 2H); 7.19 (d, 2H); 7.32-7.53 (m, 5H); 7.82 (d, 2H); 7.89 (s, 1H); 8.02 (d, 1H); 8.32 (d, 1H); 12.78 (br s, 1H).

Sources & evidence

ORD record
ord-09de79a0aa5f4315b0ef983b99f18fcc
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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