Trifluoroacetic acid → HCID 117727721, compound

HRID 1772673Notes

Reaction equation

HRID 1772673 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.COC1C=CC(C[N:36]2[C:41](=[O:42])[N:40]([CH3:43])[C:39]3[CH:44]=[CH:45][C:46](B4OC(C)(C)C(C)(C)O4)=[CH:47][C:38]=3[S:37]2(=[O:58])=[O:57])=CC=1.[C:61]([OH:67])([C:63]([F:66])([F:65])[F:64])=[O:62]>>[F:64][C:63]([F:66])([F:65])[C:61]([OH:67])=[O:62].[CH3:43][N:40]1[C:39]2[CH:44]=[CH:45][C:46]([C:2]3[N:7]4[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]5[CH:22]=[CH:21][C:20]6[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=6)[N:14]=5)[N:10]=[C:6]4[C:5]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[N:4][CH:3]=3)=[CH:47][C:38]=2[S:37](=[O:58])(=[O:57])[NH:36][C:41]1=[O:42]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 131734680HCID 131734680, compound

Product 1

HCID 117727721HCID 117727721, compound

Procedure

Compound 2b was subjected to Suzuki coupling conditions using the methods described in Example 1, Step G, with compound 40b and the resulting product was deprotected with TFA at 70° C. for 30 min. The reaction mixture was allowed to cool to rt and concentrated. The residue obtained was dried under reduced pressure overnight, suspended in ETOAc (10 mL) and sonicated for 10 min. The solid formed was collected by suction filtration and dried under reduced pressure to obtain the title compound 24. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.67-8.78 (m, 1H), 8.04-8.23 (m, 7H), 7.88-7.98 (m, 1H), 7.65-7.78 (m, 3H), 7.51 (s, 1H), 4.33 (br. s., 4H), 3.78-3.91 (m, 4H), 3.51 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customwas dried under reduced pressure overnight
  4. customsonicated for 10 min
  5. customThe solid formed
  6. filtrationwas collected by suction filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-a21fbcbd9c184df7b208dd19a3b47073
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…