1-Methoxy-2-propanol → HCID 66710771, compound

HRID 1262024Notes

Reaction equation

HRID 1262024 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([NH:13][C:14]3[C:15]([N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])=[N:16][CH:17]=[CH:18][CH:19]=3)[N:6]2[N:5]=1)=O.[CH2:26]1[N:31]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:30][CH2:29][O:28][CH2:27]1.C(N(CC)C(C)C)(C)C.COCC(O)C>>[CH3:25][N:20]([C:15]1[C:14]([NH:13][C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:38][C:35]4[CH:34]=[CH:33][C:32]([N:31]5[CH2:26][CH2:27][O:28][CH2:29][CH2:30]5)=[CH:37][CH:36]=4)=[N:5]3)=[CH:10][CH:11]=2)=[CH:19][CH:18]=[CH:17][N:16]=1)[S:21]([CH3:24])(=[O:23])=[O:22]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 81531DiisopropylethylamineHCID 66711088HCID 66711088, compound

Product 1

HCID 66710771HCID 66710771, compound

Procedure

N-[3-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-ylamino)-pyridin-2-yl]-N-methyl-methanesulfonamide (50.0 mg, 0.131 mmol), 4-(4-morpholino)aniline (46.8 mg, 0.263 mmol) and N,N-Diisopropylethylamine (0.0687 mL, 0.394 mmol) were dissolved in 1-Methoxy-2-propanol (0.500 mL, 5.12 mmol). The reaction was irradiated at 300 watts, 200° C. for 20 minutes. The reaction was then reduced en vacuo and the resulting residue was isolated and purified by Gilson prep HPLC to afford N-Methyl-N-{3-[2-(4-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-ylamino]-pyridin-2-yl}-methanesulfonamide as a lyophilized powder. (M+H)=495.1. 1H NMR (400 MHz, DMSO, d6) δ 9.26 (s, 1H), 8.77 (s, 1H), 8.03 (m, 2H), 7.52 (d, 2H, J=8.05 Hz), 7.41 (d, 1H, J=8.24 Hz), 7.33 (m, 1H), 6.91 (m, 3H), 6.76 (m, 1H), 3.78 (m, 4H), 3.25 (s, 3H), 3.21 (s, 3H), 3.07 (m, 4H).

Workup

  1. customThe reaction was irradiated at 300 watts, 200° C. for 20 minutes
  2. customthe resulting residue was isolated
  3. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-36d7773e6ae74a91b25a7e56c3a1241c
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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