1-(Chloromethyl)-4-methanesulfonylbenzene → HCID 178493824, compound

HRID 536244Notes

Reaction equation

HRID 536244 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]([CH2:22][CH2:23][N:24]=3)[C:15]([NH2:21])=[N:16][C:17]=2[C:18]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCC1C=C[C:30]([S:33](C)(=[O:35])=[O:34])=CC=1>>[CH3:20][O:19][C:18]1[C:17]2[N:16]=[C:15]([NH2:21])[N:14]3[CH2:22][CH2:23][N:24]=[C:13]3[C:12]=2[CH:11]=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:33]([CH3:30])(=[O:35])=[O:34])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 1784938207-methoxy-8-phenylmethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine2×

Product 1

HCID 178493824HCID 178493824, compound

Procedure

The procedure used for the preparation of Example 1 was used to prepare the title compound from 5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-ol bistrifluoroacetate salt (Intermediate A) and 1-(chloromethyl)-4-(methylsulfonyl)benzene. High vacuum drying gave the title compound (970 mg, 56%): HPLC MS RT=1.59 min, MH+=401.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.21 (3H, s), 3.85 (3H, s), 4.16-4.19 (2H, m), 4.32-4.35 (2H, m), 5.47 (2H, s), 7.36 (1H, d), 7.74 (2H, d), 7.88 (1H, d), 7.97 (2H, d).

Workup

  1. customThe procedure used for the preparation of Example 1

Sources & evidence

ORD record
ord-cd31b2a42a1745df8900449f4f6183e9
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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