Hydrochloric Acid → {2-Amino-6-[2-(3-aminopyrrolidine-1-carbonyl)phenyl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

HRID 1037684Notes

Reaction equation

HRID 1037684 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:43]=[CH:42][CH:41]=[CH:40][C:24]=3[C:25]([N:27]3[CH2:31][CH2:30][CH:29]([NH:32]C(=O)OC(C)(C)C)[CH2:28]3)=[O:26])[CH:8]=2)[N:3]=1.Cl>O1CCOCC1>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:43]=[CH:42][CH:41]=[CH:40][C:24]=3[C:25]([N:27]3[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28]3)=[O:26])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67367412Tert-butyl (1-{2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzoyl}pyrrolidin-3-yl)carbamate

Product 1

HCID 46701229{2-Amino-6-[2-(3-aminopyrrolidine-1-carbonyl)phenyl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product is obtained analogously to “A34” by reaction of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzoic acid with tert-butyl pyrrolidin-3-ylcarbamate. The resultant tert-butyl (1-{2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzoyl}pyrrolidin-3-yl)carbamate is treated directly with 1 M HCl in dioxane, causing the protecting group to be cleaved. The purification is carried out by means of column chromatography;

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-a8eb97830aea43f8a1daaad9c42a59a4
Source dataset
uspto-grants-2013_10
Patent number
US08546565B2

Reaction notes

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