Triethylamine → HCID 90410669, compound

HRID 589125Notes

Reaction equation

HRID 589125 reaction equation
C(N(CC)CC)C.[N:8]1([C:15]2[N:23]3[C@@H:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:25][O:26][C:21]4=[C:22]3[C:17](=[CH:18][CH:19]=[C:20]4[C:33]3[C:34]([CH3:39])=[N:35][O:36][C:37]=3[CH3:38])[N:16]=2)[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.CO>[CH3:39][C:34]1[C:33]([C:20]2[C:21]3[O:26][CH2:25][C@H:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[N:23]4[C:15]([N:8]5[CH2:14][CH2:13][CH2:12][N:11]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:10][CH2:9]5)=[N:16][C:17]([C:22]=34)=[CH:18][CH:19]=2)=[C:37]([CH3:38])[O:36][N:35]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90409126HCID 90409126, compound

Product 1

HCID 90410669HCID 90410669, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (8.1 μL, 0.058 mmol) was added to a solution of (4S)-2-(1,4-diazepan-1-yl)-7-(3,5-dimethylisoxazol-4-yl)-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazine (5.0 mg, 0.012 mmol) in methylene chloride (0.44 mL), and the mixture was cooled to 0° C. Methanesulfonyl chloride (1.8 μL, 0.023 mmol) was then added and the mixture was stirred for 5 min at 0° C. The mixture was diluted with methanol and purified by preparative LCMS using pH 10 buffer to give the title compound (3.8 mg, 64%). LCMS calc. for C25H29N6O4S (M+H)+: m/z=509.2. found: 509.2.

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-b343dbadc057455db42311599796626b
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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