Formic Acid → HCID 68551362, compound

HRID 2388575Notes

Reaction equation

HRID 2388575 reaction equation
C(O)=O.Cl[S:5]([N:8]=C=O)(=[O:7])=[O:6].[Si:11]([O:18][C@@H:19]([CH3:44])[C@@H:20]([NH:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([Cl:42])[C:35]=1[CH3:43])[C:21]1[O:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[N:24][N:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[2H]C(C(C([2H])([2H])[2H])=O)([2H])[2H]>ClCCl.CN(C)C(=O)C.C(OCC)(=O)C>[S:5](=[O:6])(=[O:7])([O:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[O:22][C:21]([C@H:20]([NH:33][C:34]3[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([Cl:42])[C:35]=3[CH3:43])[C@@H:19]([O:18][Si:11]([C:14]([CH3:16])([CH3:17])[CH3:15])([CH3:13])[CH3:12])[CH3:44])=[N:25][N:24]=2)=[CH:31][CH:30]=1)[NH2:8]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 70918Chlorosulfonyl isocyanateHCID 522220Acetone-D6HCID 136355216HCID 136355216, compound

Product 1

HCID 68551362HCID 68551362, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Procedure

To a 50 mL round bottomed flask, a mixture of formic acid (413 mg, 8.99 mmol) and N,N-dimethyl acetamide (30 mg, 0.09 mmol) was added to a stirred solution of chlorosulfonyl isocyanate (0.77 mL, 8.91 mmol) in dichloromethane (5 mL) at 42° C. The mixture was placed under reflux for 15 min and then cooled to ambient temperature. The resulting mixture was added to a stirred solution of 4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (346 mgs, 0.90 mmol) in N,N-dimethyl acetamide (6 mL) at ambient temperature. The mixture was then stirred for 17 h and then poured onto water (15 mL). Ethyl acetate (30 mL) was added to the mixture and the phases were partitioned. The organic phase was washed with water (12 mL) (×2), dried (Na2SO4) and concentrated to furnish a pale yellow oil (385 mg, yield not determined). 1H NMR (Acetone d6, 500 MHz) inter alia δ 8.07 (d, J=9 Hz, 2H), 7.53-7.47 (m, 3H), 6.84 (d, J=9 Hz, 2H), 5.53 (d, J=9 Hz, 1H), 5.22-5.17 (m, 1H), 4.77-4.68 (m, 1H), 2.37 (s, 3H) and 1.46 (d, J=6 Hz, 3H).

Workup

  1. temperatureunder reflux for 15 min
  2. additionpoured onto water (15 mL)
  3. customthe phases were partitioned
  4. washThe organic phase was washed with water (12 mL) (×2)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto furnish a pale yellow oil (385 mg
  8. customyield not

Sources & evidence

ORD record
ord-89ecf5d02b0f43e98825a119c1ebca5b
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

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