Hydrochloric Acid → HCID 71283620, compound

HRID 1752420Notes

Reaction equation

HRID 1752420 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][N:8]([C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)[N:16]=[C:15]([C:33]([NH2:35])=[O:34])[CH:14]=2)[S:9]([CH3:12])(=[O:11])=[O:10])[CH2:4][O:3]1.C(Cl)Cl.CO.Cl.O>O1CCOCC1>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][N:8]([C:13]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)[N:16]=[C:15]([C:33]([NH2:35])=[O:34])[CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226129Dichloromethane methanolHCID 71285538HCID 71285538, compound

Product 1

HCID 71283620HCID 71283620, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 6-(N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methyl sulfonamido)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxamide (0.308 g, 0.596 g) in 85:15 DCM/MeOH (5 mL) was added 4M HCl in dioxane (1.0 mL). After 1 hour, water (0.5 mL) was added and a solid formed. After 1 hour, the solid was filtered and washed successively twice with 2 mL DCM, twice with 1 mL MeOH, once with 3 mL MeOH, and twice with 1 mL DCM. The solid was dried under vacuum at 40° C. to give 6-(N-(2,3-dihydroxypropyl)methylsulfonamido)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxamide as a white powder (0.200 g, 0.420 mmol, 70% yield). 1H NMR (400 MHz, DMSO-d6): 8.63-8.54 (3H, m), 8.01 (1H, s), 7.84 (1H, s), 7.33-7.26 (2H, m), 7.23-7.17 (2H, m), 7.09 (2H, d, J=8.8 Hz), 5.08 (1H, d, J=5.5 Hz), 4.80 (1H, t, J=5.7 Hz), 4.31-4.24 (1H, m), 4.05-3.96 (1H, m), 3.86-3.77 (1H, m), 3.54 (3H, s), 3.45-3.35 (2H, m). LC/MS: m/z=477.1 [M+H]+.

Workup

  1. customa solid formed
  2. waitAfter 1 hour
  3. filtrationthe solid was filtered
  4. washwashed successively twice with 2 mL DCM, twice with 1 mL MeOH, once with 3 mL MeOH
  5. customThe solid was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-eb760ecbadd8493abaa7d75cedf035f1
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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