Potassium Acetate → HCID 66711071, compound

HRID 1262078Notes

Reaction equation

HRID 1262078 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([O:30][CH3:31])[CH:24]=3)[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS([C:35]1[N:40]=[CH:39][C:38]2=[CH:41][CH:42]=[C:43]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[O:50][CH3:51])[N:37]2[N:36]=1)=O.C([O-])(=O)C.[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:35]4[N:40]=[CH:39][C:38]5=[CH:41][CH:42]=[C:43]([C:44]6[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=6[O:50][CH3:51])[N:37]5[N:36]=4)=[C:25]([O:30][CH3:31])[CH:24]=3)[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazineHCID 66711883HCID 66711883, compound

Product 1

HCID 66711071HCID 66711071, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-[1-(4-Amino-3-methoxy-phenyl)-piperidin-4-yl]-piperazine-1-carboxylic acid benzyl ester (0.62 g, 0.0015 mol), 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.3 g, 0.0009 mol) and Potassium acetate (0.59 g, 0.0060 mol) in N,N-Dimethylformamide (10 mL) was heated at 110° C. for 40 hr. The solvent was evaporated and the residue chromatographed on silica gel prep plates 2× with ethyl acetate-IPA (20-1) giving 4-(1-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-4-yl)-piperazine-1-carboxylic acid benzyl ester as a tan solid (0.51 g, 9%). MP: 75-76° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 8.80 (s, 1H), 7.84-7.81 (d, 1H, J=8.40 Hz), 7.48 (s, 1H), 7.45-7.35 (m, 7H), 7.20 (s, 1H), 7.18 (s, 1H), 7.12-7.02 (t, 1H), 6.95-6.89 (q, 2H, J=4.68 Hz), 6.62 (d, 1H), 6.38-6.35 (q, 1H) 5.08 (s, 2H), 3.83 (s, 3H), 3.78 (s, 3H), 3.70-3.65 (d, 2H), 3.39 (br, 8H), 2.70-2.51 (m, 3H), 1.87-1.78 (m, 2H), 1.60-1.52 (m. 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed on silica gel prep plates 2× with ethyl acetate-IPA (20-1)

Sources & evidence

ORD record
ord-5b63cfd379d24e92b909fc1ccf219499
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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