Methanesulfonamide → HCID 86703786, compound

HRID 1849908Notes

Reaction equation

HRID 1849908 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH:17]=[CH:16][CH2:15]2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:20][S:21]([NH2:24])(=[O:23])=[O:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH:17]=[CH:16][CH2:15]2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:24][S:21]([CH3:20])(=[O:23])=[O:22])=[O:8]

Participants

7

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86703785HCID 86703785, compound

Product 1

HCID 86703786HCID 86703786, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-chloro-4-(cyclohex-3-en-1-ylmethoxy)-2-fluorobenzoic acid (53 mg), methanesulfonamide (35 mg), HBTU (95 mg), and DIPEA (0.13 mL) in dichloromethane (0.83 mL) was stirred at rt for 4 hr. Diluted with EtOAc, the contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (2×) and brine, and dried (Na2SO4). The crude was purified with HPLC. LCMS (Method D): RT=5.62 min, m/z: 362.1 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 12.07 (s, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.26 (d, J=12.4 Hz, 1H), 5.69 (d, J=2.1 Hz, 2H), 4.06 (dd, J=6.5, 1.3 Hz, 2H), 2.28-1.97 (m, 4H), 1.98-1.76 (m, 2H), 1.50-1.29 (m, 1H).

Workup

  1. washthe contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. customThe crude was purified with HPLC

Sources & evidence

ORD record
ord-67356f647558442399897f711dcda605
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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