Morpholine → 4-[4-Iodo-2-[(5-quinoxalinylsulfonyl)amino]benzoyl]-morpholine

HRID 230052Notes

Reaction equation

HRID 230052 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[C:6]([NH:8][S:9]([C:12]2[C:17]3=[N:18]S[N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.CN(C(ON1N=N[C:39]2C=CC=N[C:38]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1SN=C2C(S(NC3C=C(I)C=CC=3C(O)=O)(=O)=O)=CC=CC=12.N1CCOCC1>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[C:6]([NH:8][S:9]([C:12]2[C:17]3[N:18]=[CH:38][CH:39]=[N:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1

Participants

5

Reactant 4

HCID 8083MorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 160906642-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acidHCID 160906944-[2-[(2,1,3-Benzothiadiazol-4-ylsulfonyl)amino]-4-iodobenzoyl]-morpholine

Product 1

HCID 113529714-[4-Iodo-2-[(5-quinoxalinylsulfonyl)amino]benzoyl]-morpholine

Procedure

Benzo[1,2,5]thiadiazole-4-sulfonic acid [5-iodo-2-(morpholine-4-carbonyl)-phenyl]-amide. The title compound was prepared from the HATU-mediated coupling of 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodobenzoic acid and morpholine and purified as described in EXAMPLE 1, Step K. MS (ESI): mass calculated for C17H15IN4O4S2, 530.0; m/z found, 531 [M+H]+, 553 [M+Na]+. HPLC (reverse phase): RT=8.50 min. 1H NMR (400 MHz, CDCl3): (rotameric broadening) 8.91 (s, 1H), 8.31 (dd, J=7.0, 0.9 Hz, 1H), 8.27 (dd, J=8.8, 0.9 Hz, 1H), 7.97 (d, J=1.5 Hz, 1H), 7.74 (dd, J=8.8, 7.0 Hz, 1H), 7.41 (dd, J=8.1, 1.6 Hz, 1H), 6.78 (d, J=8.1 Hz, 1H), 3.75-3.05 (br m, 8H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-23925e0f844f4d2c88a69b0030522282
Source dataset
uspto-grants-2009_07
Patent number
US07563895B2

Reaction notes

Loading…