Benzyl Alcohol → HCID 135410969, compound

HRID 601406Notes

Reaction equation

HRID 601406 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:16][C:17]1[CH:45]=[CH:44][C:20]2[NH:21][C:22]([C:27]3[C:28](=[O:43])[N:29]([CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])[C:30]4[C:35]([C:36]=3[OH:37])=[CH:34][CH:33]=[CH:32][N:31]=4)=[N:23][S:24](=[O:26])(=[O:25])[C:19]=2[CH:18]=1.C(N(CC)CC)C.Cl>ClCCl>[OH:37][C:36]1[C:35]2[C:30](=[N:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH2:38][CH2:39][CH:40]([CH3:41])[CH3:42])[C:28](=[O:43])[C:27]=1[C:22]1[NH:21][C:20]2[CH:44]=[CH:45][C:17]([NH:16][S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:15][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:7])=[CH:18][C:19]=2[S:24](=[O:25])(=[O:26])[N:23]=1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1354307103-(7-Amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-(3-methylbutyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 135410969HCID 135410969, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of chlorosulfonyl isocyanate (24.5 μL, 0.281 mmol) in dichloromethane (2 mL) was treated dropwise with benzyl alcohol (29 μL, 0.281 mmol) at 25° C., stirred at 25° C. for 30 min, treated with a solution of the product of Example 205 (100 mg, 0.234 mmol) and triethylamine (130 μL, 0.936 mmol) in dichloromethane (3 mL)and stirred for 2 hrs at 25° C. The reaction mixture was treated with dichloromethane (10 mL) and 1N aqueous hydrochloric acid (10 mL). The resulting organic layer was separated and dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide the title compound (122 mg, 81%). MS (ESI−) m/z 639 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 0.99 (d, J=6.6 Hz, 6H), 1.59 (m, 2H), 1.66 (m, 1H), 4.49 (m, 2H), 5.12 (s, 2H), 7.32 (m, 5H), 7.48 (m, 2H), 7.65 (d, J=2.2 Hz, 1H), 7.75 (d, J=8.8 Hz, 1H), 8.57 (dd, J=7.7, 1.8 Hz, 1H), 8.90 (dd, J=0.8, 1.8 Hz, 1H), 11.17 (s, 1H), 12.19 (bs, 1H), 14.11 (bs, 1H).

Workup

  1. stirringstirred for 2 hrs at 25° C
  2. customThe resulting organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-474790246e5248e0b4d1a86ea898c35a
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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