Sulfuric Acid → HCID 67994889, compound

HRID 2361417Notes

Reaction equation

[C:1]([C:3]1[C:8]2[NH:9][C:10]3[CH:11]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:14][C:15]=3[C:7]=2[C:6]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N:26]3[C:35](=[O:36])[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[CH:27]3)[C:21]=2[CH3:37])=[N:5][CH:4]=1)#[N:2].S(=O)(=O)(O)[OH:39]>>[CH3:19][O:18][C:16]([C:12]1[CH:13]=[CH:14][C:15]2[C:7]3[C:6]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N:26]5[C:35](=[O:36])[C:34]6[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=6)[N:28]=[CH:27]5)[C:21]=4[CH3:37])=[N:5][CH:4]=[C:3]([C:1](=[O:39])[NH2:2])[C:8]=3[NH:9][C:10]=2[CH:11]=1)=[O:17]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 67994760HCID 67994760, compound

Product 1

HCID 67994889HCID 67994889, compound

Conditions

Temperature: 60 °C

Procedure

A stirred mixture of methyl 4-cyano-1-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-5H-pyrido[4,3-b]indole-7-carboxylate (0.192 g, 0.395 mmol) and 90% aqueous Sulfuric acid (2.000 ml, 36.8 mmol) was heated at 60° C. for 15-30 minutes. HLC-MS showed complete conversion to the desired product plus the corresponding carboxylic acid. The reaction mixture was cooled to 0° C. and neutralized to approx. pH=5-6 with 50% NaOH solution then stirred overnight. The reaction mixture was filtered and the residue dried overnight under vacuum to give methyl-4-carbamoyl-1-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-5H-pyrido[4,3-b]indole-7-carboxylate a tan/brown solid [0.111 g, 0.220 mmol, 56% yield]. The product had an HPLC Retention Time=2.798 minutes[mixture of isomers] [4 min grad, 10% MeOH/water to 90% MeOH/water, 0.1% TFA, YMC Comb screen ODS-A, 4.6×50 mm, 220 nM]; LC/MS+1 504.4

Sources & evidence

ORD record: ord-a7138a8ee71e4908998d249209ab7ead
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

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