Diisopropylethylamine → N-(3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-nicotinamide

HRID 888157Notes

Reaction equation

HRID 888157 reaction equation
F[C:2]1[N:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[S:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=2[CH:17]=1)=[O:5].Cl.[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][C:31]([CH2:32][NH2:33])=[C:26]2[CH:25]=[CH:24]1.CCN(C(C)C)C(C)C>CC(O)(C)C>[O:16]=[C:13]1[NH:12][C:11]2[CH:17]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:18]=[CH:19][CH:20]=[N:21][C:2]=3[NH:33][CH2:32][C:31]3[CH:30]=[CH:29][N:28]=[C:27]4[NH:23][CH:24]=[CH:25][C:26]=34)[CH:8]=[CH:9][C:10]=2[S:15][CH2:14]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 692636392-fluoro-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-nicotinamideHCID 69265141{1H-pyrrolo[2,3-b]pyridin-4-yl}methanamine hydrochloride

Product 1

HCID 16224616N-(3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-nicotinamide

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
170 °C

Procedure

To an oven-dry microwave tube was added 2-fluoro-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-nicotinamide (150 mg, 0.5 mmol), C-(1H-pyrrolo[2,3-b]pyridin-4-yl)-methylamine hydrochloride salt (220 mg, 1.0 mmol), DIEA (1 mL), and t-BuOH (2 mL). The resulting mixture was sealed off and underwent microwave heating at 170° C. for 20 min. Solvent was removed in vacuo. The crude solid was purified by chromatography on silica gel. Elution with DCM:MeOH mixture (97:3) gave final compound. MS (ES+): 430.6 (M+H). Calc'd. for C22H18N6O2S—430.49.

Workup

  1. customThe resulting mixture was sealed off
  2. customSolvent was removed in vacuo
  3. customThe crude solid was purified by chromatography on silica gel
  4. washElution with DCM

Sources & evidence

ORD record
ord-bb59d298e2cd4796b83c6b760088a642
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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