3-(Morpholin-4-yl)aniline → HCID 57399415, compound

HRID 1261926Notes

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.[N:21]1([C:27]2[CH:28]=[C:29]([NH2:33])[CH:30]=[CH:31][CH:32]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN1CCCC1=O>[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:33][C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:28]=3)=[N:5]2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 140 °C

Procedure

2-Methane sulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75.0 mg, 0.000261 mol) and 3-Morpholin-4-yl-phenylamine (93.0 mg, 0.000522 mol) were dissolved in N-Methylpyrrolidinone (2.0 mL) and the reaction was heated at 140° C. 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 9.70 mg of [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-morpholin-4-yl-phenyl)-amine as a lyophilated powder. (M+H)=402.20. 1H NMR (400 MHz, DMSO, d6) δ 9.23 (s, 1H), 8.94 (s, 1H), 7.70 (d, 1H, J=7.84 Hz), 7.46 (m, 1H), 7.34 (s, 1H), 7.19 (d, 1H, J=7.83 Hz), 7.08 (m, 3H), 6.90 (m, 2H), 6.87 (m, 1H), 3.75 (s, 3H), 3.63 (m, 4H), 2.83 (m, 4H).

Workup

customconsumption of starting material
customthe product was isolated
custompurified by Gilson prep HPLC

Sources & evidence

ORD record: ord-833aad3167d44cb2928bd12f1488a551
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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