N,N-Dimethylglycine → HCID 42600096, compound

HRID 908495Notes

Reaction equation

F[B-](F)(F)F.N1([O+]=C(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[C:32]1[C:33]([NH2:52])=[N:34][CH:35]=[C:36]([C:38]2[C:39]([CH2:49][O:50][CH3:51])=[N:40][N:41]([CH:43]3[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)[CH:42]=2)[CH:37]=1.[CH3:53][N:54]([CH3:59])[CH2:55][C:56](O)=[O:57].CN1CCOCC1>CN1C(=O)CCC1>[NH2:52][C:33]1[N:34]=[CH:35][C:36]([C:38]2[C:39]([CH2:49][O:50][CH3:51])=[N:40][N:41]([CH:43]3[CH2:48][CH2:47][N:46]([C:56](=[O:57])[CH2:55][N:54]([CH3:59])[CH3:53])[CH2:45][CH2:44]3)[CH:42]=2)=[CH:37][C:32]=1[C:24]1[O:23][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Benzotriazol-1-yl-[bis(dimethylamino)methylene]oxonium tetrafluoroborate (115 mg) was added to a stirred suspension of 3-(1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-piperidin-4-ylpyrazol-4-yl]pyridin-2-amine] (121 mg), 2-(dimethylamino)acetic acid (32.4 mg) and 4-methylmorpholine (0.066 ml) in NMP (1.5 ml) at 25° C. The mixture was stirred at 25° C. for 5 hours and purified by preparative HPLC using a Waters OBD reverse-phase column (C-18, 5 microns silica, 30 mm diameter, 150 mm length, flow rate of 40 ml/minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent to provide the title compound (101 mg, 69.0%). NMR Spectrum: (DMSOd6) 1.73-1.85 (m, 1H), 1.87-1.98 (m, 1H), 2.04-2.16 (m, 2H), 2.21 (s, 6H), 2.72-2.82 (m, 1H), 3.08 (d, 1H), 3.13-3.22 (m, 2H), 3.41 (s, 3H), 4.15-4.23 (m, 1H), 4.41 (s, 2H), 4.41-4.51 (m, 2H), 7.40-7.48 (m, 2H), 7.66 (bs, 2H), 7.78 (dd, 1H), 7.84 (dd, 1H), 8.23 (s, 1H), 8.43 (d, 1H), 8.50 (d, 1H); Mass spectrum: M+H+ 490.

Workup

custompurified by preparative HPLC

Sources & evidence

ORD record: ord-b67e6e77f53341bd84196f1ee5bdcc85
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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