1-Methoxy-2-propanol → HCID 66711243, compound

HRID 1262097Notes

Reaction equation

HRID 1262097 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=3)[N:6]2[N:5]=1)=O.COCC(O)C.C(OC([N:32]1[CH2:37][CH2:36][CH:35]([O:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([NH2:45])[CH:40]=2)[CH2:34][CH2:33]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C>>[CH3:18][N:16]1[CH:17]=[C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([N:32]4[CH2:33][CH2:34][CH:35]([O:38][C:39]5[CH:40]=[C:41]([NH2:45])[CH:42]=[CH:43][CH:44]=5)[CH2:36][CH2:37]4)=[N:5]3)=[CH:10][CH:11]=2)[CH:14]=[N:15]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 57803194790667-68-4HCID 667110872-Methanesulfinyl-7-(1-methyl-1H-pyrazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711243HCID 66711243, compoundYield 3%

Procedure

2-Methanesulfinyl-7-(1-methyl-1H-pyrazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazine (100.0 mg, 0.3827 mmol) was dissolved in 1-Methoxy-2-propanol (374.1 uL, 3.827 mmol) and added to 4-(3-Amino-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (223.8 mg, 0.7654 mmol) and N,N-Diisopropylethylamine (200.0 uL, 1.148 mmol). The substance was microwaved at 200 C for 15 min. The reaction was concentrated, dissolved in 1 mL of DMSO and placed onto the Gilson. Lyophilized overnight to give 3-{1-[7-(1-Methyl-1H-pyrazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-piperidin-4-yloxy}-phenylamine as a yellow solid (4 mg, 3%). LCMS (E/I+) 417 (M+H). NMR 1H (DMSO-d6)-8.82 (s, 1H), 8.39 (s, 1H), 8.16 (s, 1H), 7.24 (t, 1H, J=8.05 Hz), 7.05 (d, 1H, J=4.71 Hz), 6.87 (d, 1H, J=4.76 Hz), 6.77 (d, 1H, J=8.04 Hz), 6.69 (s, 1H), 6.65 (d, 1H, J=8.04 Hz), 4.62-4.68 (m, 1H), 4.08-4.16 (m, 2H), 3.93 (s, 3H), 3.50-3.6 (m, 2H), 2.04-2.12 (m, 2H), 1.66-1.76 (m, 2H).

Workup

  1. customThe substance was microwaved at 200 C for 15 min
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in 1 mL of DMSO

Sources & evidence

ORD record
ord-d8dc2048af62485397c76639c2d21932
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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