1-Methoxy-2-propanol → N-tert-Butyl-3-(2-{4-[4-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl]-phenylamino}-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide

HRID 1262095Notes

Reaction equation

HRID 1262095 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](S(C)=O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([C:41]3[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=3)[CH2:37][CH2:36]2)[CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C.COCC(O)C>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:47][C:44]4[CH:45]=[CH:46][C:41]([N:38]5[CH2:39][CH2:40][CH:35]([CH2:34][N:31]6[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]6)[CH2:36][CH2:37]5)=[CH:42][CH:43]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 66711063N-tert-Butyl-3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamideHCID 667119914-[4-(4-Methyl-piperazin-1-ylmethyl)-piperidin-1-yl]-phenylamine

Product 1

HCID 66711819N-tert-Butyl-3-(2-{4-[4-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl]-phenylamino}-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamideYield 30%

Procedure

N-tert-Butyl-3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (0.1 g, 0.3 mmol), 4-[4-(4-Methyl-piperazin-1-ylmethyl)-piperidin-1-yl]-phenylamine (147 mg, 0.510 mmol), N,N-Diisopropylethylamine (0.124 mL, 0.712 mmol), and 1-Methoxy-2-propanol (0.5 mL, 5 mmol) were heated in the microwave at 225° C. for 30 minutes. The reaction was concentrated and redissolved in 3 ml of DMSO and placed onto the Gilson. The most pure fractions were combined basified with sat. sodium bicarbonate, extracted with DCM, dried filtered and concentrated to give a yellow solid (47 mg, 30%). MP 233-235° C. LCMS (E/I+) 485 (M+H). NMR 1H (DMSO-d6)-9.26 (s, 1H), 8.98 (s, 1H), 8.54 (s, 1H), 8.38 (d, 1H, J=8.04 Hz), 7.84 (d, 1H, J=7.90 Hz), 7.73 (t, 1H, J=7.81 Hz), 7.57-7.61 (m, 3H), 7.16 (d, 1H, J=4.52 Hz), 6.93-6.97 (m, 3H), 3.58 (d, 2H, J=11.59 Hz), 2.54-2.62 (m, 2H), 2.28-2.38 (m, 6H), 2.14 (m, 6H), 1.77 (d, 2H, J=12.50 Hz), 1.55-1.65 (m, 1H), 1.16-1.26 (m, 3H), 1.12 (s, 9H).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in 3 ml of DMSO
  3. extractionextracted with DCM
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bcb0e849687647d7bd4bfa248000c955
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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