Dichloromethane → HCID 86630151, compound

HRID 908409Notes

Reaction equation

HRID 908409 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][CH2:19][CH2:20][OH:21])[CH:17]=2)=[CH:9][C:8]=1[C:22]1[O:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1.C(N(CC)CC)C.ClCCl>C1COCC1>[CH3:1][S:2]([O:21][CH2:20][CH2:19][CH2:18][N:16]1[CH:17]=[C:13]([C:10]2[CH:11]=[N:12][C:7]([NH2:6])=[C:8]([C:22]3[O:23][C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[N:26]=3)[CH:9]=2)[CH:14]=[N:15]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67388214HCID 67388214, compound

Product 1

HCID 86630151HCID 86630151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methanesulphonyl chloride (0.577 ml) was added to 3-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]propan-1-ol (1.25 g, Example 29-1), triethylamine (1.559 ml) dissolved dichloromethane (20 ml) and THF (20 ml) at 0° C. The resulting suspension was stirred at 25° C. for 2 hours. The suspension was filtered and washed with water (3 time) and dried over night on reduce pressure to afford 3-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]propyl methanesulphonate (0.988 g). NMR Spectrum: (DMSOd6) 2.21-2.32 (m, 2H), 3.23 (s, 3H), 4.21-4.33 (m, 4H), 7.42-7.51 (m, 2H), 7.68 (bs, 2H), 7.81 (d, 1H), 7.86 (d, 1H), 7.98 (s, 1H), 8.30 (s, 1H), 8.44 (s, 1H), 8.54 (s, 1H)

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with water (3 time)
  3. customdried over night

Sources & evidence

ORD record
ord-eefbf531cda146bb9334758641967801
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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