Phenylboronic Acid → HCID 66710807, compound

HRID 1261877Notes

Reaction equation

HRID 1261877 reaction equation
C1(B(O)O)C=CC=CC=1.CN(C)S(=O)=O.[CH3:16][O:17][CH2:18][CH2:19][N:20]1[CH2:26][CH2:25][C:24]2[CH:27]=[C:28]([NH:31][C:32]3[N:37]=[CH:36][C:35]4=[CH:38][CH:39]=[C:40]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=5[S:47]([N:50]([CH3:52])[CH3:51])(=[O:49])=[O:48])[N:34]4[N:33]=3)[CH:29]=[CH:30][C:23]=2[CH2:22][CH2:21]1.C1C=CC=CC=1B(O)O>>[CH3:16][O:17][CH2:18][CH2:19][N:20]1[CH2:26][CH2:25][C:24]2[CH:27]=[C:28]([NH:31][C:32]3[N:37]=[CH:36][C:35]4=[CH:38][CH:39]=[C:40]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=5[S:47]([N:50]([CH3:51])[CH3:52])(=[O:49])=[O:48])[N:34]4[N:33]=3)[CH:29]=[CH:30][C:23]=2[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 178486093HCID 178486093, compound

Product 1

HCID 66710807HCID 66710807, compound

Procedure

The above compound was prepared in an analogous fashion to Example 9 replacing phenylboronic acid with N,N-dimethylsulfonamide-2-benzeneboronic acid 2-{2-[3-(2-Methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-N,N-dimethyl-benzenesulfonamide as a yellow solid (22 mg, 18%). LCMS (E/I+) 521.20 (M+H). NMR 1H (DSMO-d6)-9.28 (s, 1H), 8.95 (s, 1H), 8.06 (d, 1H, J=7.53 Hz), 7.75-7.85 (m, 2H), 7.62 (d, 1H, J=8.57 Hz), 7.41 (s, 1H), 7.06 (d, 1H, J=8.25 Hz), 6.91 (d, 1H, J=4.60 Hz), 6.86 (d, 1H, J=4.56 Hz), 6.81 (d, 1H, J=8.09 Hz), 3.44 (t, 2H, J=5.64 Hz), 3.25 (s, 3H), 2.40-2.80 (bm, 10H), 2.32 (s, 3H).

Sources & evidence

ORD record
ord-70dd0da437ab4fae8638dc3feaf9217e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…