Hydrochloric Acid → HCID 59380385, compound

HRID 2353833Notes

Reaction equation

HRID 2353833 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](Cl)=[N:12][CH:11]=[N:10][C:9]=3[S:15][C:4]=2[CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([NH2:32])[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1.Cl>O1CCOCC1.CC(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13]([NH:32][C:19]4[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=5)=[C:17]([Cl:16])[CH:18]=4)=[N:12][CH:11]=[N:10][C:9]=3[S:15][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 59380405HCID 59380405, compound

Product 1

HCID 59380385HCID 59380385, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

7-Bromo-4-chloro[1]benzothieno[2,3-d]pyrimidine (7.00 g, 23.4 mmol), 3-chloro-4-(3-fluoro-benzyloxy)-phenylamine (5.88 g, 23.4 mmol), and HCl in dioxane (1 mL, 4.0 M) were heated to reflux in IPA (140 mL) for 3 days. The suspension was filtered to collect a light tan solid. The solid was re-suspended in EtOAc (350 mL) and treated with satd NaHCO3 (350 mL) to generate two clear phases. The organic phase was washed with water (350 mL), collected, dried with sodium sulfate, filtered, concentrated on a rotavap, and finally placed under high vacuum to yield an off-white solid (10.34 g, 86%). 1H NMR (DMSO-d6) δ 9.06 (s, 1H), 8.53 (s, 1H), 8.49 (d, 1H), 8.43 (s, 1H), 7.74 (d, 1H), 7.71 (s, 1H), 7.50 (d, 1H), 7.47-7.42 (m, 1H), 7.32-7.16 (m, 4H), 5.26 (s, 2H), LCMS RT=4.42 min, [M+H]+=514.3.

Workup

  1. filtrationThe suspension was filtered
  2. customto collect a light tan solid
  3. additiontreated with satd NaHCO3 (350 mL)
  4. washThe organic phase was washed with water (350 mL)
  5. customcollected
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated on a rotavap

Sources & evidence

ORD record
ord-8571b5aa92ed45faa56acf413f716ca1
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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