1-Methoxy-2-propanol → HCID 66710970, compound

HRID 1262017Notes

Reaction equation

HRID 1262017 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.[NH2:30][C:31]1[CH:32]=[CH:33][C:34]2[O:45][C:38]3([CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]3)[CH:37]=[CH:36][C:35]=2[CH:46]=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]([CH:42]3[CH2:43][C:38]4([CH:37]=[CH:36][C:35]5[CH:46]=[C:31]([NH2:30])[CH:32]=[CH:33][C:34]=5[O:45]4)[CH2:39][CH2:40][N:41]3[CH3:44])=[N:5]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 574160981'-Methylspiro[1-benzopyran-2,4'-piperidin]-6-amineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66710970HCID 66710970, compoundYield 12.8%

Procedure

2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (87.49 mg, 0.0003045 mol), N,N-Diisopropylethylamine (0.175 mL, 0.00100 mol) and 6-amino-1′-methyl-spiro(2H-1-benzopyran-2,4′-piperidine) (0.141 g, 0.000609 mol) were dissolved in 1-Methoxy-2-propanol (0.350 mL, 0.00358 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 17.67 mg of 7-(2-methoxy-phenyl)-pyrrolo(2,1-f)(1,2,4)triazin-2-yl-6-amino-1′-methyl-spiro(2H-1-benzopyran-2,4′-piperidine) as a lyophilized powder. (M+H)=456.1. 1H NMR (400 MHz, DMSO, d6) δ 9.19 (s, 1H), 8.91 (s, 1H), 7.81 (d, 1H, J=7.24 Hz), 7.57 (m, 1H), 7.45 (m, 1H), 7.34 (m, 1H), 7.21 (m, 1H), 7.11 (m, 1H), 6.90 (d, 2H, J=7.65 Hz), 6.70 (d, 1H, J=8.56 Hz), 3.79 (s, 3H), 3.33 (m, 2H), 3.18 (m, 2H), 2.83 (m, 3H), 2.62 (m, 2H), 1.92 (m, 2H), 1.79 (m, 4H).

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-095df70c94034356a29fed6542fa29fb
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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