Ethanolamine → HCID 19379097, compound

HRID 2210607Notes

Reaction equation

HRID 2210607 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[NH:19][CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1.N1C=CC=C(C2N3C=CC([C:47](C4C5C(=CC(OCC6C=CC=CC=6)=CC=5)NC=4)=[O:48])=C3CS2)C=1.[CH2:66]([CH2:68][NH2:69])[OH:67].[K+].[Br-]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([C:47](=[O:48])[NH:69][CH2:68][CH2:66][OH:67])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 253877Potassium BromideHCID 10717912HCID 10717912, compoundHCID 15292729HCID 15292729, compound

Product 1

HCID 19379097HCID 19379097, compound

Procedure

The desired compound was prepared according to the method of Example 37 except substituting 3-(pyridin-3-yl)-7-[6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole, prepared as in Example 28, for 3-(Pyridin-3-yl)-7-(6-phenylmethoxyindol-3-yl)carbonyl-1H,3H-pyrrolo[1,2-c]thiazole, and substituting ethanolamine for amounts. 1H NMR (DMSO-d6, 300 MHz) δ3.32-3.42 (m, 2H), 3.60 (q, 2H, J=6Hz), 4.51 (d, 1H, J=15Hz), 4.68 (dd, 1H, J=2, 15Hz), 4.88 (t, 1H, J=6Hz), 6.79 (d, 1H, J=3Hz), 6.81 (d, 1H, J=1Hz), 7.09 (d, 1H, J=3Hz,) 7.32 (t, 2H, J=9 Hz), 7.45 (dd, 1H, J=5, 8 Hz), 7.61 (dd, 1H, J=1, 8 Hz), 7.69 (dt, 1H, J=1, 8 Hz), 7.71-7.76 (m, 2H), 8.32 (d, 1H, J=8 Hz), 8.51 (d, 1H, J=1 Hz). 8.56-8.61 (m, 3H), 8.47 (t, 1H, J=6 Hz). MS (FAB) m/e 527 (M+H)+, 440. IR (KBr) 1701, 1601, 1530, 1510, 1475, Anal calcd for C29H23FN4O3S: C, 66.15; H, 4.40; N, 10.64. Found: C, 64.93; H, 4.14; N, 10.00.

Sources & evidence

ORD record
ord-d025725046a74565a9abae3df916114f
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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