Ethanesulfonamide → HCID 86703781, compound

HRID 1849903Notes

Reaction equation

HRID 1849903 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18][O:19][C:20]2[C:28]([CH:29]3[CH2:31][CH2:30]3)=[CH:27][C:23]([C:24]([OH:26])=O)=[C:22]([F:32])[CH:21]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([S:35]([NH2:38])(=[O:37])=[O:36])[CH3:34].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>ClCCCl>[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18][O:19][C:20]2[C:28]([CH:29]3[CH2:30][CH2:31]3)=[CH:27][C:23]([C:24]([NH:38][S:35]([CH2:33][CH3:34])(=[O:37])=[O:36])=[O:26])=[C:22]([F:32])[CH:21]=2)[CH2:15]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 73702EthanesulfonamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867037804-((1-Benzhydrylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 86703781HCID 86703781, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 4-((1-benzhydrylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid (35.6 mg), ethanesulfonamide (22.5 mg), HBTU (41.9 mg), and DIPEA (0.073 mL) in DCE (0.83 mL) was heated at 35° C. for 16 hr then at 55° C. for 1 hr. More ethyanesulfonamide (9 mg) was added. Heating continued for 1 hr. Added with 1M NaH2PO4, the contents were extracted with DCM (2×). The combined extracts were dried (Na2SO4). The crude was purified with HPLC (23 mg). LCMS (Method D): RT=5.08 min, m/z: 523.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 11.78 (s, 1H), 7.49-7.36 (m, 4H), 7.28 (dd, J=8.3, 6.8 Hz, 4H), 7.22-7.09 (m, 3H), 6.95 (d, J=12.8 Hz, 1H), 4.49 (s, 1H), 4.21 (d, J=6.2 Hz, 2H), 3.47-3.36 (m, 2H), 3.02 (s, 2H), 2.93-2.81 (m, 1H), 2.10-1.99 (m, 1H), 1.22 (t, J=7.5 Hz, 3H), 0.95-0.82 (m, 2H), 0.71-0.61 (m, 2H).

Workup

  1. additionMore ethyanesulfonamide (9 mg) was added
  2. temperatureHeating
  3. waitcontinued for 1 hr
  4. extractionthe contents were extracted with DCM (2×)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customThe crude was purified with HPLC (23 mg)

Sources & evidence

ORD record
ord-2951f399415f4bba8f59f1bdb39b10da
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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