Methanesulfonyl chloride → HCID 70651420, compound

HRID 2361427Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[C:12]([N:13]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14]2)=[CH:11][CH:10]=[CH:9][C:8]=1[C:24]1[CH:32]=[CH:31][C:30]([C:33]([NH2:35])=[O:34])=[C:29]2[C:25]=1[C:26]1[CH2:39][NH:38][CH2:37][CH2:36][C:27]=1[NH:28]2>>[CH3:6][C:7]1[C:12]([N:13]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14]2)=[CH:11][CH:10]=[CH:9][C:8]=1[C:24]1[CH:32]=[CH:31][C:30]([C:33]([NH2:35])=[O:34])=[C:29]2[C:25]=1[C:26]1[CH2:39][N:38]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:37][CH2:36][C:27]=1[NH:28]2

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 67994842HCID 67994842, compound

Product 1

HCID 70651420HCID 70651420, compoundYield 34%

Procedure

Using the procedure of Example 43 but substituting methanesulfonyl chloride in place of acetic anhydride, 9-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-6-carboxamide (20 mg, 0.044 mmol) was converted into the desired product as a white solid (8.0 mg, 34% yield). LCMS (M+H)+ m/z 528.2, (M+Na)+550.2. 1H NMR (400 MHz, DMSO-d6) δ 8.40, 8.15 (1 H, 2s), 8.22 (1 H, ddd, J=13.9, 8.1, 1.3 Hz), 7.92 (1 H, t, J=7.8 Hz), 7.79 (1 H, dd, J=7.6, 4.5 Hz), 7.73 (1 H, t, J=8.3 Hz), 7.54-7.67 (2 H, m), 7.51 (1 H, t, J=7.7 Hz), 7.43 (1 H, dd, J=7.2, 5.6 Hz), 6.83-7.00 (1 H, m), 3.43-3.86 (3 H, m), 3.28-3.34 (3 H, m), 2.89-3.19 (3 H, m), 1.74 (3 H, 2s).

Sources & evidence

ORD record: ord-eaece453891f4f6d9f44a77a838cccd9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

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