Dichloromethane → N-{2-[2-(2-Methoxy-4-piperazin-1-ylmethyl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide

HRID 1262305Notes

Reaction equation

HRID 1262305 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[N:27]=[CH:26][C:25]4=[CH:28][CH:29]=[C:30]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[N:37]([S:39]([CH3:42])(=[O:41])=[O:40])[CH3:38])[N:24]4[N:23]=3)=[C:17]([O:43][CH3:44])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)Cl.FC(F)(F)C(O)=O>>[CH3:44][O:43][C:17]1[CH:16]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:20]=[CH:19][C:18]=1[NH:21][C:22]1[N:27]=[CH:26][C:25]2=[CH:28][CH:29]=[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N:37]([CH3:38])[S:39]([CH3:42])(=[O:41])=[O:40])[N:24]2[N:23]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 667120714-(4-{7-[2-(Methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-3-methoxy-benzyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66711969N-{2-[2-(2-Methoxy-4-piperazin-1-ylmethyl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamideYield 98%

Procedure

Into a 8-dram vial, 4-(4-{7-[2-(Methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-3-methoxy-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (0.450 g, 0.724 mmol), Methylene chloride (15 mL, 230 mmol), and Trifluoroacetic Acid (3 mL, 40 mmol) were added. The reaction was stirred at room temperature overnight. The reaction was partitioned with saturated NaHCO3 and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum to give N-{2-[2-(2-Methoxy-4-piperazin-1-ylmethyl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide as an orange solid (0.37 g, 98%). LCMS (E/I+) 522.12 (M+H). NMR 1H (DMSO-d6)-8.95 (s, 1H), 7.95-7.99 (m, 1H), 7.87 (d, 1H, J=7.99 Hz), 7.72 (s, 1H), 7.60-7.67 (m, 1H), 7.50-7.57 (m, 2H), 7.07 (d, 1H, J=4.59 Hz), 6.96 (d, 1H, J=4.59 Hz), 6.93 (s, 1H), 6.72 (d, 1H, J=7.94 Hz), 3.83 (s, 3H), 3.37 (s, 3H), 3.04 (s, 3H), 2.88 (s, 3H), 2.73 (t, 4H, J=4.02 Hz), 2.29 (bs, 4H).

Workup

  1. customThe reaction was partitioned with saturated NaHCO3 and DCM
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2b0d5f5b887a47e7978a57c69f008e53
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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