Hydrochloric Acid → 6-(3-Dimethylamino-propoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime

HRID 1853303Notes

Reaction equation

HRID 1853303 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[O:10][C:9]([C:18]2[N:23]=[CH:22][N:21]3[CH:24]=[CH:25][CH:26]=[C:20]3[CH:19]=2)=[CH:8]1)(C)(C)C.Cl.[Cl:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33].Cl>C(O)(C)C>[CH3:33][N:32]([CH3:34])[CH2:31][CH2:30][CH2:29][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:18]1[N:23]=[CH:22][N:21]3[CH:24]=[CH:25][CH:26]=[C:20]3[CH:19]=1)=[CH:8][C:7]2=[N:6][OH:5].[ClH:28].[CH3:33][N:32]([CH3:34])[CH2:31][CH2:30][CH2:29][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:18]1[N:23]=[CH:22][N:21]3[CH:24]=[CH:25][CH:26]=[C:20]3[CH:19]=1)=[CH:8][C:7]2=[N:6][OH:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 866730736-Hydroxy-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl-oxime

Product 2

HCID 759645286-(3-Dimethylamino-propoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oximeHCID 866730726-(3-Dimethylamino-propoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6-(3-Dimethylamino-propoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime was prepared in 22% overall yield using the procedure described in example 42A, starting from 6-hydroxy-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime (example 81A) and (3-Chloro-propyl)-dimethyl-amine hydrochloride. The compound was treated with a 1.25 N solution of hydrogen chloride in isopropanol to yield 6-(3-Dimethylamino-propoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime hydrochloride as an orange solid.

Workup

  1. customoverall yield

Sources & evidence

ORD record
ord-b4e2cc76e9e143e499b4714d4c2b00c9
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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