Ammonia → HCID 131729557, compound

HRID 1040922Notes

Reaction equation

HRID 1040922 reaction equation
COC1C(N)=C[C:6]2[N:12]([CH3:13])[CH2:11][CH2:10][CH2:9][NH:8][C:7]=2C=1.[CH3:16][O:17][CH:18](O)[CH3:19].Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:31][C:30]=2[O:41][CH3:42])[C:25]([Cl:43])=[CH:24][N:23]=1.C[C:45]1([CH3:58])[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O.C(=O)([O-])[O-].[NH3:63]>CO.ClCCl>[Cl:43][C:25]1[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:31][C:30]=2[O:41][CH3:42])=[N:27][C:22]([NH:63][C:45]2[C:18]([O:17][CH3:16])=[CH:19][C:7]3[CH2:8][NH:9][CH2:10][CH2:11][N:12]([CH3:13])[C:6]=3[CH:58]=2)=[N:23][CH:24]=1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 19660Carbonate IonHCID 65617D-Camphorsulfonic AcidHCID 30156371-MethoxyethanolHCID 67264377HCID 67264377, compoundHCID 86633851(2,5-Dichloropyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amine

Product 1

HCID 131729557HCID 131729557, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 40 ml sure-seal reaction vial, 8-methoxy-5-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylamine (0.21 g, 1 mmole), methoxy ethanol (6 ml), and (2,5-Dichloro-pyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amine (0.30 g, 0.8 mmole), DL-10_camphorsulfonic acid (0.47 g, 2 mmoles) were added. The reaction was heated to reflux for 3 hours. Upon cooling to room temperature, Methanol (10 ml) and MP-carbonate (0.70 g, 2.2 mmoles) were added. The reaction was stirred for one hour. The solid was filtered and washed with methanol. The solvent was removed under vacuum to afford a red solid. The product (0.18 g, 34% yield) was isolated via column chromatography with dichloromethane and ammonia in methanol (2% to 30% ammonia in methanol) as eluant. NMR 1H-(CDCl3)-δ-8.28 (d, 1H, J=8.08 Hz), 8.06 (s, 1H), 8.05 (bs, 1H), 7.57 (bs, 1H), 7.40 (bs, 1H), 6.72 (bs, 1H), 6.55 (bs, 1H), 6.54 (d, 1H, J=9.60 Hz), 3.93 (s, 3H), 3.88-3.92 (m, 6H), 3.87 (s, 3H), 3.16 (t, 4H, J=4.55 Hz), 3.06-3.18 (m, 2H), 2.90-2.94 (m, 2H), 2.74 (s, 3H). LCMS (ESI+) 527.45 (M+H)

Workup

  1. customTo 40 ml sure-seal
  2. customreaction vial
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 3 hours
  5. filtrationThe solid was filtered
  6. washwashed with methanol
  7. customThe solvent was removed under vacuum
  8. customto afford a red solid

Sources & evidence

ORD record
ord-56eec9921a814f4ebfddb1fac1958096
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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