1-Methoxy-2-propanol → HCID 66711132, compound

HRID 1262001Notes

Reaction equation

HRID 1262001 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.C(N(CC)C(C)C)(C)C.[N:30]1([CH:36]2[CH2:41][CH2:40][CH2:39][N:38]([C:42]3[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=3)[CH2:37]2)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.COCC(O)C>>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:48][C:45]3[CH:46]=[CH:47][C:42]([N:38]4[CH2:39][CH2:40][CH2:41][CH:36]([N:30]5[CH2:31][CH2:32][O:33][CH2:34][CH2:35]5)[CH2:37]4)=[CH:43][CH:44]=3)=[N:5]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazineHCID 66711339HCID 66711339, compound

Product 1

HCID 66711132HCID 66711132, compoundYield 36.3%

Procedure

2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (100.0 mg, 0.0003480 mol), N,N-Diisopropylethylamine (0.0909 mL, 0.000522 mol) and 4-(3-Morpholin-4-yl-piperidin-1-yl)-phenylamine (0.182 g, 0.000696 mol) were dissolved in 1-Methoxy-2-propanol (0.99 mL, 0.010 mol) and the reaction was irradiated at 300 watts, 180° C. for 40 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 61.16 mg of [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(3-morpholin-4-yl-piperidin-1-yl)-phenyl]-amine as a lyophilized powder. (M+H)=486.3. 1H NMR (400 MHz, DMSO, d6) δ 9.20 (m, 1H), 8.92 (s, 1H), 7.84 (dd, 1H, J=1.67, 5.97 Hz), 7.61 (d, 2H, J=9.00 Hz), 7.45 (m, 1H), 7.21 (d, 1H, J=8.00 Hz), 7.15 (m, 1H), 6.91 (m, 4H), 4.33 (m, 2H), 3.77 (s, 3H), 3.74 (m, 2H), 3.42 (m, 3H), 2.90 (m, 2H), 2.67 (m, 2H), 2.13 (m, 2H), 1.75 (m, 2H), 1.61 (m, 2H).

Workup

  1. customthe reaction was irradiated at 300 watts, 180° C. for 40 minutes or until HPLC
  2. customconsumption of starting material
  3. customthe product was isolated
  4. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-93c86d443f3f4ed5acd47958968ade02
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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