Hydrochloric Acid → HCID 66896808, compound

HRID 541912Notes

Reaction equation

HRID 541912 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[CH:10]=[C:11]([CH:29]=[CH:30][CH:31]=1)[CH2:12][S:13][C:14]1[CH:15]=[C:16]([NH:20][C:21]2[C:26]([Cl:27])=[CH:25][N:24]=[C:23](Cl)[N:22]=2)[CH:17]=[CH:18][CH:19]=1.Cl>COCCO.C(O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:27][C:26]1[CH:25]=[N:24][C:23]2[NH:8][C:9]3[CH:31]=[CH:30][CH:29]=[C:11]([CH:10]=3)[CH2:12][S:13][C:14]3[CH:15]=[C:16]([NH:20][C:21]=1[N:22]=2)[CH:17]=[CH:18][CH:19]=3

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86636289HCID 86636289, compound

Product 1

HCID 66896808HCID 66896808, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
150 °C

Procedure

A solution of N-{3-[(3-aminobenzyl)thio]phenyl}-2,5-dichloropyrimidin-4-amine trifluoroacetate (33 mg, 67 μmol) in 2-methoxyethanol (6.6 mL) was treated with 3.5 M HCl in ethanol (3 mL) and heated in the microwave at 150° C. for 5 min. The reaction mixture was degassed to remove the HCl and concentrated to a crude residue. This material was purified by preparative LCMS to give the desired product (8.4 mg, 27%) as a TFA salt. LCMS for C17H14ClN4S (M+H)+: m/z=341.0. 1H NMR (300 MHz, DMSO-d6): δ 9.59 (s, 1H), 9.20 (s, 1H), 8.17 (s, 2H), 7.93 (s, 1H), 7.21-7.15 (m, 3H), 7.08-7.05 (m, 1H), 7.00-6.97 (m, 1H), 6.91-6.88 (m, 1H), 4.03 (s, 2H).

Workup

  1. customThe reaction mixture was degassed
  2. customto remove the HCl
  3. concentrationconcentrated to a crude residue
  4. customThis material was purified by preparative LCMS

Sources & evidence

ORD record
ord-302be6239390481898ab032f911a35e8
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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