Dimethylformamide → HCID 59239574, compound

HRID 1697946Notes

Reaction equation

HRID 1697946 reaction equation
CNC(N1CCC2[C:11]([N:15]3[CH2:20][CH2:19]OC[CH2:16]3)=[N:10]C(C3C=CC([N+]([O-])=O)=CC=3)=NC=2C1)=S.[N+:30]([C:33]1[CH:38]=[CH:37][C:36]([C:39]2[N:40]=[C:41]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)[C:42]3[CH2:48][CH2:47][NH:46][CH2:45][C:43]=3[N:44]=2)=[CH:35][CH:34]=1)([O-])=O.N(C)=[C:56]=S.[CH3:59][N:60]([CH:62]=[O:63])C>O>[CH2:59]([NH:60][C:62]([NH:30][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[N:40]=[C:41]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)[C:42]3[CH2:48][CH2:47][N:46]([C:11]4[N:15]([CH3:16])[CH:20]=[CH:19][N:10]=4)[CH2:45][C:43]=3[N:44]=2)=[CH:35][CH:34]=1)=[O:63])[CH3:56]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 11167Methyl isothiocyanate2×HCID 59239067HCID 59239067, compoundHCID 59239124HCID 59239124, compound

Product 1

HCID 59239574HCID 59239574, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step 1—Synthesis of N-methyl-4-morpholino-2-(4-nitrophenyl)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carbothioamide (mn): To a solution of 4-(2-(4-nitrophenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)morpholine (lr) (486 mg, 1.4 mmol) in DMF (15 mL) was added dropwise a solution of isothiocyanatomethane (208 mg, 2.8 mmol) in DMF (3 mL) at rt. After 3.5 hrs, LCMS showed reaction proceeded slowly. Additional isothiocyanatomethane (104 mg) was added. It was stirred at rt for 48 hrs. It was diluted with H2O. The solid was filtered off, washed with H2O, dried to afford 443 mg (75%) desired compound mn as a light yellow solid. 1H NMR (500 MHz, DMSO) δ 8.58-8.53 (m, 2H), 8.38-8.33 (m, 2H), 7.93 (d, J=4.2, 1H), 4.91 (s, 2H), 4.04 (t, J=5.1, 2H), 3.77-3.72 (m, 4H), 3.59-3.54 (m, 4H), 2.96 (d, J=4.1, 3H), 2.76 (t, J=5.1, 2H). LC-MS: m/z=+415 (M+H)+.

Workup

  1. customreaction
  2. filtrationThe solid was filtered off
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-ba2c4cad90504e2aaaa79f1c401342b6
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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