Acetic Acid → HCID 66711613, compound

HRID 1262083Notes

Reaction equation

HRID 1262083 reaction equation
C(OC([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:30]4[N:35]=[CH:34][C:33]5=[CH:36][CH:37]=[C:38]([C:39]6[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=6[O:45][CH3:46])[N:32]5[N:31]=4)=[C:25]([O:47][CH3:48])[CH:24]=3)[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.Br.CC(O)=O>>[CH3:46][O:45][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[C:38]1[N:32]2[C:33]([CH:34]=[N:35][C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([N:20]4[CH2:21][CH2:22][CH:17]([N:14]5[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]5)[CH2:18][CH2:19]4)=[CH:24][C:25]=3[O:47][CH3:48])=[N:31]2)=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 66711071HCID 66711071, compound

Product 1

HCID 66711613HCID 66711613, compoundYield 41.7%

Procedure

A mixture of 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 (0.027 g, 0.042 mmol) and 33% wt. HBr in HOAc (4 mL, 40 mmol) was stirred at room temperature for 5 hours. The reaction was evaporated under vacuum. Water (5 mL) was added and the solution filtered. The filtrate was basified, extracted with ethyl acetate, washed dried and evaporated to give a tan solid (0.009 g, 40%). MP; 65-67° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 8.88 (s, 1H), 7.84-7.81 (d, 2H, J=8.84 Hz), 7.48 (s, 1H), 7.43-7.41 (t, 1H, J=7.58 Hz), 7.21-7.19 (d, 1H, J=8.20 Hz), 7.10-7.06 (t, 1H, J=7.24 Hz), 6.95-6.89 (q, 2H, J=4.60 Hz), 6.63 (s, 1H), 6.38-6.36 (d, 1H, J=8.60 Hz), 3.83 (s, 3H), 3.78 (s, 3H), 3.69-3.62 (br, 2H), 2.76 (br, 3H) 2.67-2.57 (m, 3H), 2.35-2.25 (br, 2H), 1.90 (s, 1H), 1.89-1.78 (br, 2H), 1.53 (br, 3H), 1.23 (m, 4H), 1.19-1.18 (d, 2H, J=5.36 Hz) 1.13-1.08 (q, 4H, J=7.00 Hz), 0.95-0.83 (m, 5H).

Workup

  1. customThe reaction was evaporated under vacuum
  2. additionWater (5 mL) was added
  3. filtrationthe solution filtered
  4. extractionextracted with ethyl acetate
  5. washwashed
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ea0742f78bba45ad89be2766c924983e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…