Hydrochloric Acid → N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine hydrochloride

HRID 222029Notes

Reaction equation

HRID 222029 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][C:13]4([CH2:18][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1)[O:17][CH2:16][CH2:15][O:14]4.[Cl:19][C:20]1[CH:21]=[C:22]([NH2:34])[CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.Cl>C(O)C>[ClH:1].[Cl:19][C:20]1[CH:21]=[C:22]([NH:34][C:2]2[C:3]3[C:10]4[CH2:11][CH2:12][C:13]5([CH2:18][C:9]=4[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[O:17][CH2:16][CH2:15][O:14]5)[CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineHCID 179901054-chloro-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolane]

Product 1

HCID 67313375N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To ethanol (60 mL) were sequentially added 4-chloro-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2′-[1,3]dioxolane] (5.70 g, 20.2 mmol), 3-Chloro-4-(pyridin-2-ylmethoxyl)-phenylamine (4.78 g, 20.37 mmol), and HCl in ethanol (1N, 4 mL). The suspension was stirred with heating to 80° C., upon which time the contents turn brown and homogeneous. After 12 h, the dark orange-yellow heterogeneous mixture was removed from heating, and allowed to cool to rt. The contents were concentrated down to about 30 mL in volume and the precipitate was collected by filtration as a light-brown solid (10.1 g, 92%). 1H-NMR (DMSO-d6) δ 8.71 (d, 1H), 8.40 (s, 1H), 8.33 (s, 1H), 8.10 (td, 1H), 7.80 (d, 1H), 7.75 (d, 1H), 7.56 (m, 2H), 7.25 (d, 1H), 5.48 (br, 1H), 5.38 (s, 2H), 3.99 (s, 4H), 3.28 (t, 2H), 3.03 (s, 2H), 1.97 (t, 2H); LCMS RT=2.73 min; [M+H]+=481.1.

Workup

  1. customthe dark orange-yellow heterogeneous mixture was removed
  2. temperaturefrom heating
  3. temperatureto cool to rt
  4. concentrationThe contents were concentrated down to about 30 mL in volume
  5. filtrationthe precipitate was collected by filtration as a light-brown solid (10.1 g, 92%)

Sources & evidence

ORD record
ord-40f1b435b6134c4a9af675c46f21d483
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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