Methanesulfonyl chloride → HCID 178505248, compound

HRID 536276Notes

Reaction equation

HRID 536276 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[C:9]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)[N:8]3[CH2:21][CH2:22][N:23]=[C:7]3[C:6]=2[CH:5]=[CH:4][C:3]=1[O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>>[CH3:34][S:35]([O:1][C:2]1[C:11]2[N:10]=[C:9]([NH:12][C:13]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:20])[N:8]3[CH2:21][CH2:22][N:23]=[C:7]3[C:6]=2[CH:5]=[CH:4][C:3]=1[O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1)(=[O:37])=[O:36]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178522494HCID 178522494, compound2×

Product 1

HCID 178505248HCID 178505248, compound

Procedure

The procedure used for the preparation of Example 36 was used to prepare the title compound from N-[7-hydroxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]nicotinamide (Intermediate H) and methanesulfonyl chloride (58 mg, 49%). TLC: Rf=0.38 in 10% MeOH/CH2Cl2, HPLC MS RT=2.05 min, [M+Na]+=551; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.18-2.30 (2H, m), 3.03-3.17 (2H, m), 3.28-3.37 (2H, m), 3.44-3.54 (2H, m), 3.60-3.75 (5H, m), 3.95-4.05 (2H, m), 4.19-4.29 (2H, m), 4.40 (2H, t), 4.56-4.66 (2H, m), 7.63 (1H, d), 7.82 (1H, dd), 8.29 (1H, d), 8.64 (1H, d), 8.93 (1H, dd), 9.35 (1H, s).

Workup

  1. customThe procedure used for the preparation of Example 36

Sources & evidence

ORD record
ord-3a636897ee8c4d4b8cf3814c7b8ac979
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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