N,N-Dimethylglycine → HCID 58529840, compound

HRID 1972993Notes

Reaction equation

HRID 1972993 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH2:39]([O:46][C:47]1[CH:48]=[C:49]([C:54]2[CH:55]=[C:56]([CH:64]3[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]3)[N:57]3[C:62]=2[C:61]([NH2:63])=[N:60][CH:59]=[N:58]3)[CH:50]=[C:51]([F:53])[CH:52]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:39]([O:46][C:47]1[CH:48]=[C:49]([C:54]2[CH:55]=[C:56]([CH:64]3[CH2:69][CH2:68][N:67]([C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[CH2:66][CH2:65]3)[N:57]3[C:62]=2[C:61]([NH2:63])=[N:60][CH:59]=[N:58]3)[CH:50]=[C:51]([F:53])[CH:52]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58529821HCID 58529821, compound

Product 1

HCID 58529840HCID 58529840, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of N,N-dimethylglycine (100 mg, 0.24 mmol) in DCM (1 mL) was treated with N,N-diisopropylethylamine (83 uL, 0.48 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (55 mg, 0.29 mmol) and 1-hydroxybenzotriazole (38.8 mg, 0.29 mmol) followed by 5-[3-(benzyloxy)-5-fluorophenyl]-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (100 mg, 0.24 mmol). The mixture was stirred at rt overnight then purified by HPLC. 20 mg (17%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 7.91 (s, 1H), 7.47-7.35 (m, 5H), 6.88 (s, 1H), 6.82 (d, 1H), 6.75 (d, 1H), 6.50 (s, 1H), 5.49 (s, 2H), 5.13 (s, 2H), 4.66 (d, 1H), 4.23 (d, 1H), 3.48 (m, 1H), 3.25-3.15 (m, 2H), 3.12-3.04 (m, 1H), 2.76 (td, 1H), 2.29 (s, 6H), 2.17 (s, 2H), 1.72-1.61 (m, 2H); LC-MS m/z [M+H]+ 503.3, RT 2.34 min.

Workup

  1. customthen purified by HPLC

Sources & evidence

ORD record
ord-0a767baac92049bfb06f8f8c5ac4187f
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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