Trimethyl orthoformate → HCID 66970456, compound

HRID 1363131Notes

Reaction equation

HRID 1363131 reaction equation
COC1C=C(OC)C=CC=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20]([NH:22][C@H:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=3)[O:26][CH2:25][CH2:24]2)[C:19]([NH2:34])=[CH:18][N:17]=1.O.[C:42]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC)(OC)OC>CO>[F:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[O:26][CH2:25][CH2:24][C@H:23]2[N:22]1[CH:42]=[N:34][C:19]2[C:20]1=[N:21][C:16]([N:15]1[C:8]3[CH:9]=[C:10]([C:11]#[N:12])[CH:13]=[CH:14][C:7]=3[N:6]=[CH:5]1)=[N:17][CH:18]=2

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 66970399HCID 66970399, compound

Product 1

HCID 66970456HCID 66970456, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a microwave vial was added the above amine, a catalytic amount of para-toluene sulfonic acid monohydrate, trimethyl orthoformate (0.5 mL) and MeOH (1 mL). The vial was capped and heated in an Emrys™ Optimizer microwave at 150.degree C. for 5 minutes. The mixture was concentrated in vacuo, and purified by RP HPLC to yield 4.6 mg of the titled product as the TFA salt, NMR CDCl3 1H δ 9.5 (br s, 1H), 9.3 (s, 1H), 9.0 (s, 1H), 8.2 (br s, 1H), 8.0 (d, 1H), 7.7 (d, 1H), 7.1-7.0 (m, 2H), 6.6 (dd, 1H), 6.0 (t, 1H), 4.4 (m, 1H), 4.3 (m, 1H), 2.7 (m, 2H); 19F δ −121, −76 ppm; MH+=412.

Workup

  1. customThe vial was capped
  2. temperatureheated in an Emrys™ Optimizer microwave at 150.degree C
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by RP HPLC

Sources & evidence

ORD record
ord-cc66240bfc50423baf4b30d859b93c40
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…