4-Methylmorpholine → HCID 57382978, compound

HRID 2168251Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[CH3:37][C:38]1[C:46]2[C:45]([N:47]3[CH2:52][CH2:51][CH:50]([NH2:53])[CH2:49][CH2:48]3)=[N:44][CH:43]=[N:42][C:41]=2[NH:40][CH:39]=1>CC#N>[CH3:37][C:38]1[C:46]2[C:45]([N:47]3[CH2:52][CH2:51][CH:50]([NH:53][C:12](=[O:14])[C:11]4[CH:15]=[CH:16][CH:17]=[C:9]([O:8][CH2:7][CH2:6][N:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)[CH:10]=4)[CH2:49][CH2:48]3)=[N:44][CH:43]=[N:42][C:41]=2[NH:40][CH:39]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-{[2-(1-pyrrolidinyl)ethyl]oxy}benzoic acid D38 (200 mg) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (171 mg, 0.98 mmol) was dissolved under argon in MeCN (20 ml) and cooled down to 0° C. Then N-methylmorpholine (0.3 ml) was added and the mixture was stirred at 0° C. for 2 hours. To this mixture was added 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine hydrochloride D11 (240 mg) in small portions, afterwards the reaction was then warmed up to room temperature. After stirring for 16 hours, the reaction was filtered and concentrated to give crude product. This product was purified by prep-HPLC (A 0.01% NH4HCO3/Water, B: ACN, 0˜8 min 25-50%, 50%˜60% 8-12 min, 60%˜95% 12-15 min, 95˜95% 15-18 min) to give 50 mg of white solid of desired product E43. LCMS [MH+] [email protected] min (5 min run)

Workup

temperatureafterwards the reaction was then warmed up to room temperature
stirringAfter stirring for 16 hours
filtrationthe reaction was filtered
concentrationconcentrated
customto give crude product
customThis product was purified by prep-HPLC (A 0.01% NH4HCO3/Water, B

Sources & evidence

ORD record: ord-75664db2928a4d52b6cc279216131b61
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045485B2

Reaction notes

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